Ortho-substituted aryl amides for controlling invertebrate pests

ABSTRACT

Disclosed are compounds of Formula I, their N-oxides and agriculturally suitable salts 
                         
wherein
         J is a phenyl ring, a 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused carbobicyclic or heterobicyclic ring system wherein each ring or ring system is substituted with from one to four substituents independently selected from R 5 ;   K is —NR 1 C(=A)-, —N═C(GR 6 )— or —NR 1 SO 2 —;   L is —C(═B)NR 2 —, —C(GR 6 )═N—, —SO 2 NR 2 —, —C(═B)O— or —C(═B)—; and   A, B, G, R 1 , R 2 , R 3 , R 4 , R 5 , R 6  and n are as defined in the disclosure.       
     Also disclosed are methods for controlling invertebrate pests comprising contacting the pests or their environment with a biologically effective amount of a compound of Formula I and compositions containing the compounds of Formula I. Intermediate compounds useful in preparing the compounds of Formula I are also disclosed.

BACKGROUND OF THE INVENTION

This invention relates to certain ortho-substituted aryl amides, theirN-oxides, salts and compositions suitable for agronomic and nonagronomicuses, including those listed below, and methods of their use forcontrolling invertebrate pests in both agronomic and nonagronomicenvironments.

The control of invertebrate pests is extremely important in achievinghigh crop efficiency. Damage by invertebrate pests to growing and storedagronomic crops can cause significant reduction in productivity andthereby result in increased costs to the consumer. The control ofinvertebrate pests in forestry, greenhouse crops, ornamentals, nurserycrops, stored food and fiber products, livestock, household, and publicand animal health is also important. Many products are commerciallyavailable for these purposes, but the need continues for new compoundsthat are more effective, less costly, less toxic, environmentally saferor have different modes of action.

NL 9202078 discloses N-acyl anthranilic acid derivatives of Formula i asinsecticides

wherein, inter alia, X is a direct bond; Y is H or C₁-C₆ alkyl; Z isNH₂, NH(C₁-C₃ alkyl) or N(C₁-C₃ alkyl)₂; and R¹ through R⁹ areindependently H, halogen, C₁-C₆ alkyl, phenyl, hydroxy, C₁-C₆ alkoxy orC₁-C₇ acyloxy.

SUMMARY OF THE INVENTION

This invention pertains to compounds of Formula I, and N-oxides andsalts thereof

wherein

-   -   J is a phenyl ring, a 5- or 6-membered heteroaromatic ring or an        aromatic 8-, 9- or 10-membered fused carbobicyclic or        heterobicyclic ring system wherein each ring or ring system is        substituted with from one to four substituents independently        selected from R⁵;    -   K is —NR¹C(=A)-, —N═C(GR⁶)— or —NR¹SO₂—;    -   L is —C(═B)NR²—, —C(GR⁶)═N—, —SO₂NR²—, —C(═B)O— or —C(═B)—;    -   A and B are independently O, S, NR⁸, NOR⁸, NN(R⁸)₂, S═O, N—CN or        N—NO₂;    -   each G is independently O, S or NR⁸;    -   R¹ is H; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆        cycloalkyl each optionally substituted with one or more        substituents independently selected from the group consisting of        halogen, CN, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄        alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₂-C₄ alkoxycarbonyl, C₁-C₄        alkylamino, C₂-C₈ dialkylamino and C₃-C₆ cycloalkylamino; or    -   R¹ is C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆        alkylaminocarbonyl or C₃-C₈ dialkylaminocarbonyl;    -   R² is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆        cycloalkyl, C₁-C₄ alkoxy, C₁-C₄ alkylamino, C₂-C₈ dialkylamino,        C₃-C₆ cycloalkylamino, C₂-C₆ alkoxycarbonyl or C₂-C₆        alkylcarbonyl;    -   R³ is H; C₁-C₄ alkoxy; C₁-C₄ alkylamino; C₂-C₈ dialkylamino;        C₃-C₆ cycloalkylamino; C₂-C₆ alkoxycarbonyl or C₂-C₆        alkylcarbonyl; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or        C₃-C₆ cycloalkyl, each optionally substituted with one or more        substituents independently selected from the group consisting of        halogen, CN, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄        alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₂-C₆        alkoxycarbonyl, C₂-C₆ alkylcarbonyl, C₃-C₆ trialkylsilyl, and a        phenyl, phenoxy or 5- or 6-membered heteroaromatic ring, each        ring optionally substituted with from one to three substituents        independently selected from R⁹; or    -   R² and R³ can be taken together with the nitrogen to which they        are attached to form a ring containing 2 to 6 atoms of carbon        and optionally one additional atom selected from the group        consisting of nitrogen, sulfur and oxygen, said ring optionally        substituted with from one to four substituents independently        selected from the group consisting of C₁-C₂ alkyl, halogen, CN,        NO₂ and C₁-C₂ alkoxy;    -   each R⁴ is independently C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆        alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl,        C₂-C₆ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂,        hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄        alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄        haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄ alkylamino,        C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, or C₃-C₆        trialkylsilyl; or    -   each R⁴ is independently a phenyl, benzyl or phenoxy ring, each        ring optionally substituted with from one to three substituents        independently selected from R⁹;    -   each R⁵ is independently H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆        alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl,        C₂-C₆ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, CO₂H,        CONH₂, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄        alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄        haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl,        C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino,        C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆        alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl, C₃-C₆        trialkylsilyl; or    -   each R⁵ is independently a phenyl, benzyl, benzoyl, phenoxy or        5- or 6-membered heteroaromatic ring, or an aromatic 8-, 9- or        10-membered fused heterobicyclic ring system, each ring or ring        system optionally substituted with from one to three        substituents independently selected from R⁹; or    -   (R⁵)₂ when attached to adjacent carbon atoms can be taken        together as —OCF₂O—, —CF₂CF₂O— or —OCF₂CF₂O—;    -   each R⁶ is independently C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆        alkynyl, each optionally substituted with one or more        substituents independently selected from the group consisting of        halogen, CN, C₁-C₄ alkoxy, C₂-C₆ alkoxyalkoxy, C₁-C₄ alkylthio,        (C₃-C₆ trialkylsilyl)C₁-C₂ alkoxy or R⁷; C₃-C₆ cycloalkyl; C₂-C₆        alkylcarbonyl; C₂-C₆ alkoxycarbonyl; C₂-C₆ alkylaminocarbonyl;        C₃-C₈ dialkylaminocarbonyl; C₁-C₄ alkylsulfonyl; C₁-C₄        haloalkylsulfonyl or C₃-C₉ trialkylsilyl; or    -   each R⁶ is independently a phenyl ring or a 5- or 6-membered        heteroaromatic ring, each ring optionally substituted with from        one to three substituents independently selected from R⁹;    -   each R⁷ is independently a phenyl, benzyloxy or 5- or 6-membered        heteroaromatic ring, each ring optionally substituted with from        one to three substituents independently selected from R⁹;    -   each R⁸ is independently H; C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆        alkynyl, each optionally substituted with one or more        substituents independently selected from the group consisting of        halogen, CN, C₁-C₄ alkoxy, C₁-C₄ alkylthio or R⁷; C₃-C₆        cycloalkyl; C₂-C₆ alkylcarbonyl; C₂-C₆ alkoxycarbonyl; C₂-C₆        alkylaminocarbonyl; C₃-C₈ dialkylaminocarbonyl or C₃-C₉        trialkylsilyl; or    -   each R⁹ is independently a phenyl ring or a 5- or 6-membered        heteroaromatic ring, each ring optionally substituted with from        one to three substituents independently selected from R⁹;    -   each R⁹ is independently C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄        alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl,        C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄        alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl,        C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆        cycloalkylamino, C₄-C₈ (alkyl)cycloalkylamino, C₂-C₄        alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl,        C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl; and    -   n is 1 to 4;        provided that when K is —NR¹C(=A)- and A is O or S, then L is        other than —C(═O)NR²— or —C(═S)NR²—.

This invention also pertains to a method for controlling an invertebratepest comprising contacting the invertebrate pest or its environment witha biologically effective amount of a compound of Formula I, an N-oxidethereof or a suitable salt of the compound (e.g., as a compositiondescribed herein). This invention also relates to such a method whereinthe invertebrate pest or its environment is contacted with abiologically effective amount of a compound of Formula I, an N-oxidethereof or a suitable salt thereof, or a composition comprising thecompound, N-oxide thereof or a suitable salt thereof and a biologicallyeffective amount of at least one additional compound or agent forcontrolling an invertebrate pest.

This invention also pertains to a composition for controlling aninvertebrate pest comprising a biologically effective amount of acompound of Formula I, an N-oxide thereof or a suitable salt of thecompound and at least one additional component selected from the groupconsisting of surfactants, solid diluents and liquid diluents. Thisinvention also pertains to a composition comprising a biologicallyeffective amount of a compound of Formula I, an N-oxide thereof or asuitable salt of the compound and an effective amount of at least oneadditional biologically active compound or agent.

DETAILS OF THE INVENTION

In the above recitations, “alkyl”, used either alone or in compoundwords such as “alkylthio” or “haloalkyl” includes straight-chain orbranched alkyl, such as methyl, ethyl, n-propyl, i-propyl, or thedifferent butyl, pentyl or hexyl isomers. “Alkenyl” includesstraight-chain or branched alkenes such as 1-propenyl, 2-propenyl, andthe different butenyl, pentenyl and hexenyl isomers. “Alkenyl” alsoincludes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. “Alkynyl”includes straight-chain or branched alkynes such as 1-propynyl,2-propynyl and the different butynyl, pentynyl and hexynyl isomers.“Alkynyl” can also include moieties comprised of multiple triple bondssuch as 2,5-hexadiynyl. “Alkoxy” includes, for example, methoxy, ethoxy,n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxyisomers. “Alkylthio” includes branched or straight-chain alkylthiomoieties such as methylthio, ethylthio, and the different propylthio andbutylthio isomers. “Cycloalkyl” includes, for example, cyclopropyl,cyclobutyl, cyclopentyl and cyclohexyl. “Trialkylsilyl” includes(CH₃)₃Si, (CH₃CH₂)₃Si and [(CH₃)₃C](CH₃)₂Si.

The term “aromatic” indicates that each of the ring atoms is essentiallyin the same plane and has a p-orbital perpendicular to the ring plane,and in which (4n+2) π electrons, when n is 0 or a positive integer, areassociated with the ring to comply with Hückel's rule. The term“aromatic ring system” denotes fully unsaturated carbocycles andheterocycles in which at least one ring of a polycyclic ring system isaromatic. Aromatic carbocyclic rings or fused carbobicyclic ring systemsincludes fully aromatic carbocycles and carbocycles in which at leastone ring of a polycyclic ring system is aromatic (e.g. phenyl, naphthyland 1,2,3,4-tetrahydro-naphthyl). The term “nonaromatic carbocyclicring” denotes fully saturated carbocycles as well as partially or fullyunsaturated carbocycles where the Hückel rule is not satisfied by thering. The term “hetero” in connection with rings or ring systems refersto a ring or ring system in which at least one ring atom is not carbonand which can contain 1 to 4 heteroatoms independently selected from thegroup consisting of nitrogen, oxygen and sulfur, provided that each ringcontains no more than 4 nitrogens, no more than 2 oxygens and no morethan 2 sulfurs. The terms “heteroaromatic ling or ring system” and“aromatic fused heterobicyclic ring system” includes fully aromaticheterocycles and heterocycles in which at least one ring of a polycyclicring system is aromatic (where aromatic indicates that the Hückel ruleis satisfied). The term “nonaromatic heterocyclic ring or ring system”denotes fully saturated heterocycles as well as partially or fullyunsaturated heterocycles where the Hückel rule is not satisfied by anyof the rings in the ring system. The heterocyclic ring or ring systemcan be attached through any available carbon or nitrogen by replacementof a hydrogen on said carbon or nitrogen.

The term “halogen”, either alone or in compound words such as“haloalkyl”, includes fluorine, chlorine, bromine or iodine. Further,when used in compound words such as “haloalkyl”, said alkyl may bepartially or fully substituted with halogen atoms which may be the sameor different. Examples of “haloalkyl” include F₃C, ClCH₂, CF₃CH₂ andCF₃CCl₂. The terms “haloalkenyl”, “haloalkynyl”, “haloalkoxy”, and thelike, are defined analogously to the term “haloalkyl”. Examples of“haloalkenyl” include (Cl)₂C═CHCH₂ and CF₃CH₂CH═CHCH₂. Examples of“haloalkynyl” include HC≡CCHCl, CF₃C≡C, CCl₃C≡C and FCH₂C≡CCH₂. Examplesof “haloalkoxy” include CF₃O, CCl₃CH₂O, HCF₂CH₂CH₂O and CF₃CH₂O.

Examples of “alkylcarbonyl” include C(O)CH₃, C(O)CH₂CH₂CH₃ andC(O)CH(CH₃)₂. Examples of “alkoxycarbonyl” include CH₃OC(═O),CH₃CH₂OC(═O), CH₃CH₉CH₂OC(═O), (CH₃)₂CHOC(═O) and the different butoxy-or pentoxycarbonyl isomers. Examples of “alkylaminocarbonyl” includeCH₃NHC(═O), CH₃CH₂NHC(═O), CH₃CH₂CH₂NHC(═O), (CH₃)₂CHNHC(═O) and thedifferent butylamino- or pentylaminocarbonyl isomers. Examples of“dialkylaminocarbonyl” include (CH₃)₂NC(═O), (CH₃CH₂)₂NC(═O),CH₃CH₂(CH₃)NC(═O), CH₃CH₂CH₂(CH₃)NC(═O) and (CH₃)₂CHN(CH3)C(═O).

The total number of carbon atoms in a substituent group is indicated bythe “C_(i)-C_(j)” prefix where i and j are integers from 1 to 8. Forexample, C₁-C₃ alkylsulfonyl designates methylsulfonyl throughpropylsulfonyl; C₂ alkoxyalkyl designates CH₃OCH₂; C₃ alkoxyalkyldesignates, for example, CH₃CH(OCH₃), CH₃OCH₂CH₂ or CH₃CH₂OCH₂; and C₄alkoxyalkyl designates the various isomers of an alkyl group substitutedwith an alkoxy group containing a total of four carbon atoms, examplesincluding CH₃CH₂CH₂OCH₂ and CH₃CH₂OCH₂CH₂.

In the above recitations, when a compound of Formula I contains aheterocyclic ring, all substituents are attached to this ring throughany available carbon or nitrogen by replacement of a hydrogen on saidcarbon or nitrogen.

When a compound is substituted with a substituent bearing a subscriptthat indicates the number of said substituents can exceed 1, saidsubstituents (when they exceed 1) are independently selected from thegroup of defined substituents. Further, when the subscript indicates arange, e.g. (R)_(i-j), then the number of substituents may be selectedfrom the integers between i and j inclusive.

The term “optionally substituted” indicates that the group is eitherunsubstituted or substituted. The term “optionally substituted with fromone to three substituents” and the like indicates that from one to threeof the available positions on the group may be substituted. When a groupcontains a substituent which can be hydrogen, for example R¹ or R⁵,then, when this substituent is taken as hydrogen, it is recognized thatthis is equivalent to said group being unsubstituted.

Compounds of this invention can exist as one or more stereoisomers. Thevarious stereoisomers include enantiomers, diastereomers, atropisomersand geometric isomers. One skilled in the art will appreciate that onestereoisomer may be more active and/or may exhibit beneficial effectswhen enriched relative to the other stereoisomer(s) or when separatedfrom the other stereoisomer(s). Additionally, the skilled artisan knowshow to separate, enrich, and/or to selectively prepare saidstereoisomers. Accordingly, the compounds of the invention may bepresent as a mixture of stereoisomers, individual stereoisomers, or asan optically active form. Some compounds of this invention can exist asone or more tautomers, and all tautomeric forms of such compounds arepart of the present invention. Accordingly, the compounds of theinvention may be present as a mixture of tautomers or the individualtautomers.

The present invention comprises compounds selected from Formula I,N-oxides and suitable salts thereof. One skilled in the art willappreciate that not all nitrogen containing heterocycles can formN-oxides since the nitrogen requires an available lone pair of electronsfor oxidation to the oxide; one skilled in the art will recognize thosenitrogen containing heterocycles which can form N-oxides. One skilled inthe art will also recognize that tertiary amines can form N-oxides.Synthetic methods for the preparation of N-oxides of heterocycles andtertiary amines are very well known by one skilled in the art includingthe oxidation of heterocycles and tertiary amines with peroxy acids suchas peracetic and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide,alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate,and dioxiranes such as dimethydioxirane. These methods for thepreparation of N-oxides have been extensively described and reviewed inthe literature, see for example: T. L. Gilchrist in ComprehensiveOrganic Synthesis, vol. 7, pp 748-750, S. V. Ley, Ed., Pergamon Press;M. Tisler and B. Stanovnik in Comprehensive Heterocyclic Chemistry, Vol.3, pp 18-19, A. J. Boulton and A. McKillop, Eds., Pergamon Press; M. R.Grimmett and B. R. T. Keene in Advances in Heterocyclic Chemistry, Vol.43, pp 139-151, A. R. Katritzky, Ed., Academic Press; M. Tisler and B.Stanovnik in Advances in Heterocyclic Chemistry, Vol. 9, pp 285-291, A.R. Katritzky and A. J. Boulton, Eds., Academic Press; and G. W. H.Cheeseman and E. S. G. Werstiuk in Advances in Heterocyclic Chemistry,Vol. 22, pp 390-392, A. R. Katritzky and A. J. Boulton, Eds., AcademicPress.

The salts of the compounds of the invention include acid-addition saltswith inorganic or organic acids such as hydrobromic, hydrochloric,nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic,malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic orvaleric acids. The salts of the compounds of the invention also includethose formed with organic bases (e.g., pyridine, ammonia, ortriethylamine) or inorganic bases (e.g., hydrides, hydroxides, orcarbonates of sodium, potassium, lithium, calcium, magnesium or barium)when the compound contains an acidic group such as a carboxylic acid orphenol.

As noted above, each J is independently a phenyl ring, a 5- or6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-memberedfused carbobicyclic or heterobicyclic ring system, wherein each ring orring system is substituted with from one to four R⁵. An example ofphenyl substituted with from one to four R⁵ is the ring illustrated asU-1 in Exhibit 1 below, wherein R^(v) is R⁵ and r is an integer from 1to 4. Examples of aromatic 8-, 9- or 10-membered fused carbobicyclicring system substituted with from one to four R⁵ include a naphthylgroup illustrated as U-85 in Exhibit 1 and a 1,2,3,4-tetrahydronaphthylgroup illustrated as U-89 in Exhibit 1, wherein R^(v) is R³ and r is aninteger from 1 to 4. Examples of 5- or 6-membered heteroaromatic ringssubstituted with from one to four R⁵ include the rings U-2 through U-53illustrated in Exhibit 1 wherein R^(v) is R⁵ and r is an integer from 1to 4. Note that J-1 through J-4 below also denote 5- or 6-memberedheteroaromatic rings. Note that U-2 through U-20 are examples of J-1,U-21 through U-35 and U-40 are examples of J-2, U-41 through U-48 areexamples of J-3 and U-49 through U-53 are examples of J-4. Examples ofaromatic 8-, 9- or 10-membered fused heterobicyclic ring systemssubstituted with from one to four R⁵ include U-54 through U-84illustrated in Exhibit 1 wherein R^(v) is R⁵ and r is an integer from 1to 4.

Although R^(v) groups are shown in the structures U-1 through U-90, itis noted that when they are optional substituents they do not need to bepresent. Note that when R^(v) is H when attached to an atom, this is thesame as if said atom is unsubstituted. The nitrogen atoms that requiresubstitution to fill their valence are substituted with H or R^(v). Notethat some U groups can only be substituted with less than 4 R^(v) groups(e.g. U-14, U-15, U-18 through U-21 and U-32 through U-34 can only besubstituted with one R^(v)). Note that when the attachment point between(R^(v))_(r) and the U group is illustrated as floating, (R^(v))_(r) canbe attached to any available carbon atom of the U group. Note that whenthe attachment point on the U group is illustrated as floating, the Ugroup can be attached to the remainder of Formula I through anyavailable carbon of the U group by replacement of a hydrogen atom.

As noted above, certain R¹, R³, R⁶ and R⁸ groups can be optionallysubstituted with one or more substituents. The term “optionallysubstituted” in connection with these R^(w) groups (wherein w is 1, 3, 6or 8) refers to R groups that are unsubstituted or have at least onenon-hydrogen substituent. Examples of optionally substituted R^(w)groups are those that are optionally substituted by replacement of ahydrogen on a carbon atom of the R^(w) group with one or more (up to thetotal number of hydrogens available for replacement in any specificR^(w) group) substituents independently selected from the substituentslisted in the Summary of the Invention above. Although thesesubstituents are listed, it is noted that they do not need to be presentsince they are optional substituents. Of particular note are R^(w)groups that are unsubstituted. Of note are R^(v) groups substituted withfrom one to five substituents. Also of note are R^(w) groups substitutedwith one substituent.

As noted above, R³ can be C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl orC₃-C₆ cycloalkyl each optionally substituted with (among others) aphenyl, phenoxy or 5- or 6-membered heteroaromatic ring, each ringoptionally substituted with from one to three substituents independentlyselected from R⁹. Examples of such substituent rings include the ringsillustrated as rings U-1 (phenyl), U-2 through U-53 (5- or 6-memberedheteroaromatic rings) and U-86 (phenoxy) illustrated in Exhibit 1 above,wherein R^(v) is R⁹ and r is an integer from 1 to 3.

As noted above, each R⁴ can be independently (among others) a phenyl,benzyl or phenoxy ring, each ring optionally substituted with from oneto three substituents independently selected from R⁹. Examples of suchsubstituent rings include the rings illustrated as rings U-1 (phenyl),U-87 (benzyl) and U-86 (phenoxy) illustrated in Exhibit 1 above, whereinR^(v) is R⁹ and r is an integer from 1 to 3;

As noted above, each R⁵ can be independently (among others) a phenyl,benzyl, benzoyl, phenoxy or 5- or 6-membered heteroaromatic ring, or anaromatic 8-, 9- or 10-membered fused heterobicyclic ring system, eachring or ring system optionally substituted with from one to threesubstituents independently selected from R⁹. Examples of suchsubstituent rings include the rings illustrated as rings U-1 (phenyl),U-87 (benzyl), U-88 (benzoyl), U-86 (phenoxy), U-2 through U-53. (5- or6-membered heteroaromatic rings) and U-54 through. U-84 (aromatic 8-, 9-or 10-membered fused heterobicyclic ring systems) illustrated in Exhibit1 above, wherein R^(v) is R⁹ and r is an integer from 1 to 3.

As noted above, each R⁶ and each R⁸ can be independently (among others)a phenyl ring or a 5- or 6-membered heteroaromatic ring, each ringoptionally substituted with from one to three substituents independentlyselected from R⁹. Examples of such R⁶ each R⁸ groups include the ringsillustrated as rings U-1 (phenyl) and U-2 through U-53 (5- or 6-memberedheteroaromatic rings)illustrated in Exhibit 1 above, wherein R^(v) is R⁹and r is an integer from 1 to 3.

As noted above, each R⁷ can be independently a phenyl, benzyloxy or 5-or 6-membered heteroaromatic ring, each ring optionally substituted withfrom one to three substituents independently selected from R⁹. Examplesof such R⁷ groups include the rings illustrated as rings U-1 (phenyl),U-90 (benzyloxy) and U-2 through U-53 (5- or 6-membered heteroaromaticrings)illustrated in Exhibit 1 above, wherein R^(v) is R⁹ and r is aninteger from 1 to 3.

Preferred compounds for reasons of better activity and/or ease ofsynthesis are:

-   -   Preferred 1. Compounds of Formula I wherein K is —NR¹C(=A)- and        A is O.    -   Preferred 2. Compounds of Formula I wherein L is —C(═B)NR²— and        B is O.    -   Preferred 3. Compounds of Preferred 1 or Preferred 2 wherein        -   J is a phenyl ring or a 5- or 6-membered heteroaromatic ring            selected from the group consisting of J-1, J-2, J-3 and J-4,            each ring substituted with from one to four substituents            independently selected from R⁵

-   -   -   Q is O, S or NR⁵;        -   W, X, Y and Z are independently N or CR⁵, provided that in            J-3 and J-4 at least one of W, X, Y or Z is N;        -   R¹ is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆            cycloalkyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl;        -   R² is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆            cycloalkyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl;        -   R³ is H; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or            C₃-C₆ cycloalkyl each optionally substituted with one or            more substituents independently selected from the group            consisting of halogen, CN, C₁-C₂ alkoxy, C₁-C₂ alkylthio,            C₁-C₂ alkylsulfinyl and C₁-C₂ alkylsulfonyl;        -   one of the R⁴ groups is attached to remainder of Formula I            at either the 2-position or 5-position of the phenyl ring,            and said R⁴ is C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen, CN,            NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄            alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio,            C₁-C₄ haloalkylsulfinyl or C₁-C₄ haloalkylsulfonyl;        -   each R⁵ is independently H, C₁-C₄ alkyl, C₁-C₄ haloalkyl,            halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄            alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄            haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄            haloalkylsulfonyl, C₂-C₄ alkoxycarbonyl, C₂-C₆            alkylaminocarbonyl or C₃-C₈ dialkylaminocarbonyl; or        -   each R⁵ is independently a phenyl, benzyl or 5- or            6-membered heteroaromatic ring, each ring optionally            substituted with from one to three substituents            independently selected from R⁹; or        -   (R⁵)₂ when attached to adjacent carbon atoms can be taken            together as —OCF₂O—, —CF₂CF₂O— or —OCF₂CF₂O—;        -   each R⁶ is independently C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆            alkynyl, each optionally substituted with one or more            substituents independently selected from the group            consisting of halogen, CN, C₁-C₄ alkoxy, C₁-C₄ alkylthio and            R⁷; and        -   n is 1 or 2.

Of note are compounds of Preferred 3 wherein K is —NR¹C(═O)— and L is—C(GR⁶)═N— or —SO₂NR²—. Also of note are compounds of Preferred 3wherein K is —NR¹C(═O)— and L is —C(═O)—. Also of note are compounds ofPreferred 3 wherein L is —C(═O)NR²— and K is —N═C(GR⁶)— or —NR¹SO₂—.

-   -   Preferred 4. Compounds of Preferred 3 wherein        -   R¹ and R² are each independently H or C₁-C₄ alkyl;        -   R³ is C₁-C₄ alkyl optionally substituted with halogen, CN,            OCH₃, or S(O)_(p)CH₃;        -   each R⁵ is independently H, C₁-C₄ alkyl, C₁-C₄ haloalkyl,            halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄            alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄            haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄            haloalkylsulfonyl or C₂-C₄ alkoxycarbonyl, C₂-C₆            alkylaminocarbonyl or C₃-C₈ dialkylaminocarbonyl; or a            phenyl, benzyl, or 5- or 6-membered heteroaromatic ring,            each ring optionally substituted with halogen, CN, NO₂,            C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl,            C₁-C₄ haloalkyl, C₁-C₄ alkoxy or C₁-C₄ haloalkoxy; provided            that one R⁵ is attached to J at the position ortho to K and            at least one R⁵ is other than H;        -   G is O or S; and        -   p is 0, 1 or 2.    -   Preferred 5. Compounds of Preferred 4 wherein J is a phenyl,        pyrazole, pyrrole, pyridine or pyrimidine ring, each substituted        with one R⁵ attached to J at the position ortho to K and        optionally one or two additional R⁵.    -   Preferred 6. Compounds of Preferred 5 wherein        -   R¹ and R² are both H;        -   one R⁴ is attached to remainder of Formula I at the            2-position of the phenyl ring ortho to the K-J moiety and is            selected from the group consisting of C₁-C₃ alkyl, CF₃,            OCF₃, OCHF₂, S(O)_(p)CF₃, S(O)_(p)CHF₂ and halogen and            optionally a second R⁴ is attached at the 4-position of the            phenyl ring para to the K-J moiety and is selected from the            group consisting of halogen, C₁-C₃ alkyl and C₁-C₃            haloalkyl.    -   Preferred 7. Compounds of Preferred 6 wherein        -   J is a pyrazole or pyrrole ring selected from the group            consisting of J-5, J-6, J-7, J-8, J-9 and J-10, each ring            substituted with R⁵ and optionally substituted with R¹⁰ and            R¹¹;

-   -   -   R⁵ is H, C₁-C₄ alkyl, C₁-C₄ haloalkyl, or

-   -   -   V is N, CH, CF, CCl, CBr or CI;        -   each R¹⁰ and each R¹² is independently H, C₁-C₆ alkyl, C₃-C₆            cycloalkyl, C₁-C₆ haloalkyl, halogen, CN, C₁-C₄ alkoxy,            C₁-C₄ haloalkoxy or C₁-C₄ haloalkylthio; and        -   R¹¹ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆            haloalkenyl, C₃-C₆ alkynyl or C₃-C₆ haloalkynyl.

Note that R¹⁰ and R¹¹ are subsets of R⁵. Note that when R¹² is otherthan H it is a subset of R⁹ and that the F, Cl, Br or I atomsencompassed within V are also a subset of R⁹. Note that the moietyillustrated for R⁵ is attached to J via the bond highlighted with thewavy line.

-   -   Preferred 8. Compounds of Preferred 7 wherein V is N.    -   Preferred 9. Compounds of Preferred 7 wherein V is CH, CF, CCl        or CBr.    -   Preferred 10. Compounds of Preferred 8 or Preferred 9 wherein        -   R¹² is H, C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen or CN;        -   R¹⁰ is H, CH₃, CF₃, OCH₂CF₃, OCHF₂ or halogen; and        -   R¹¹ is CH₂CF₃, CHF₂ or CF₃.    -   Preferred 11. Compounds of Preferred 10 wherein J substituted        with R⁵ and optionally substituted with R¹⁰ is J-5; R¹² is Cl or        Br; and R¹⁰ is halogen, OCH₂CF₃, OCHF₂ or CF₃.    -   Preferred 12. Compounds of Preferred 10 wherein J substituted        with R⁵ and optionally substituted with R¹¹ is J-6; R¹² is Cl or        Br; and R¹¹ is CH₂CF₃, CHF₂ or CF₃.    -   Preferred 13. Compounds of Preferred 10 wherein J substituted        with R⁵ and optionally substituted with R¹¹ is J-7; R¹² is Cl or        Br; and R¹¹ is CH₂CF₃, CHF₂ or CF₃.    -   Preferred 14. Compounds of Preferred 10 wherein J substituted        with R⁵ and optionally substituted with R¹⁰ is J-8; R¹² is Cl or        Br; and R¹⁰ is halogen, OCH₂CF₃, OCHF₂ or CF₃.    -   Preferred 15. Compounds of Preferred 10 wherein J substituted        with R⁵ and optionally substituted with R¹⁰ and R¹ is J-9; R¹²        is Cl or Br; R¹⁰ is halogen, OCH₂CF₃, OCHF₂ or CF₃; and R¹¹ is        CH₂CF₃, CHF₂ or CF₃.    -   Preferred 16. Compounds of Preferred 10 wherein J substituted        with R⁵ and optionally substituted with R¹¹ is J-10; R¹² is Cl        or Br; and R¹¹ is CH₂CF₃, CHF₂ or CF₃.

Most preferred is the compound of Formula I that is

-   1-(3-Chloro-2-pyridinyl)-N-[2-methyl-6-[[(1-methylethyl)amino]sulfonyl]phenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide.

Of note are compounds of Formula If, their N-oxides and agriculturallysuitable salts

wherein

-   -   J is a phenyl ring, a naphthyl ring system, a 5- or 6-membered        heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused        heterobicyclic ring system wherein each ring or ring system is        optionally substituted with 1 to 4 R⁵;    -   K is —NR¹C(=A)-, —N═C(GR⁶)— or —NR¹SO₂—;    -   L is —C(═B)NR²—, —C(GR⁶)═N—, —SO₂NR²—, or —C(═O)—;    -   A and B are independently O, S, NR⁶, NOR⁶, NN(R⁶)₂, S═O, N—CN or        N—NO₂;    -   each G is independently O, S or NR⁶;    -   R¹ is H; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆        cycloalkyl each optionally substituted with one or more        substituents selected from the group consisting of halogen, CN,        NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄        alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₂-C₄ alkoxycarbonyl, C₁-C₄        alkylamino, C₂-C₈ dialkylamino and C₃-C₆ cycloalkylamino; or    -   R¹ is C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆        alkylaminocarbonyl or C₃-C₈ dialkylaminocarbonyl;    -   R² is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆        cycloalkyl, C₁-C₄ alkoxy, C₁-C₄ alkylamino, C₂-C₈ dialkylamino,        C₃-C₆ cycloalkylamino, C₂-C₆ alkoxycarbonyl or C₂-C₆        alkylcarbonyl;    -   R³ is H; C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆        cycloalkyl, each optionally substituted with one or more        substituents selected from the group consisting of halogen, CN,        NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio,        C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₂-C₆ alkoxycarbonyl,        C₂-C₆ alkylcarbonyl, C₃-C₆ trialkylsilyl, or a phenyl, phenoxy        or 5- or 6-membered heteroaromatic ring, each ring optionally        substituted with one to three substituents independently        selected from the group consisting of C₁-C₄ alkyl, C₂-C₄        alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄        haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen,        CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄        alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈        dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆        (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆        alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈        dialkylaminocarbonyl or C₃-C₆ trialkylsilyl; C₁-C₄ alkoxy; C₁-C₄        alkylamino; C₂-C₈ dialkylamino; C₃-C₆ cycloalkylamino; C₂-C₆        alkoxycarbonyl or C₂-C₆ alkylcarbonyl; or    -   R² and R³ can be taken together with the nitrogen to which they        are attached to form a ring containing 2 to 6 atoms of carbon        and optionally one additional atom of nitrogen, sulfur or        oxygen, said ring optionally substituted with 1 to 4        substituents selected from the group consisting of C₁-C₂ alkyl,        halogen, CN, NO₂ and C₁-C₂ alkoxy;    -   each R⁴ is independently H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆        alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl,        C₂-C₆ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂,        hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄        alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄        haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄ alkylamino,        C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, or C₃-C₆        trialkylsilyl; or    -   each R⁴ is independently phenyl, benzyl or phenoxy, each        optionally substituted with C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄        alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl,        C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄        alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl,        C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆        cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄        alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl,        C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl;    -   each R⁵ is independently H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆        alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl,        C₂-C₆ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, CO₂H,        CONH₂, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄        alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄        haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl,        C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino,        C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆        alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl, C₃-C₆        trialkylsilyl; or    -   each R⁵ is independently a phenyl, benzyl, benzoyl, phenoxy, 5-        or 6-membered heteroaromatic ring or an aromatic 8-, 9- or        10-membered fused heterobicyclic ring system, each ring        optionally substituted with one to three substituents        independently selected from the group consisting of C₁-C₄ alkyl,        C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl,        C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl,        halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄        alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄        alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆        (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆        alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈        dialkylaminocarbonyl or C₃-C₆ trialkylsilyl; or    -   (R⁵)₂ when attached to adjacent carbon atoms can be taken        together as —OCF₂O—, —CF₂CF₂O— or —OCF₂CF₂O—;    -   each R⁶ is independently C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆        alkynyl, optionally substituted with halogen, CN, C₁-C₄ alkoxy,        C₁-C₄ alkylthio or R⁷; C₃-C₆ cycloalkyl; or C₂-C₄        alkoxycarbonyl; or    -   each R⁶ is independently a phenyl ring or a 5- or 6-membered        heteroaromatic ring, each ring optionally substituted with one        to three substituents independently selected from the group        consisting of C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆        cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄        haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄        alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl,        C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆        cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄        alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl,        C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl;    -   each R⁷ is independently a phenyl ring or a 5- or 6-membered        heteroaromatic ring, each ring optionally substituted with one        to three substituents independently selected from the group        consisting of C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆        cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄        haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄        alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl,        C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆        cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄        alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl,        C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl; and    -   n is 1 to 4;    -   provided that when K is —NR¹C(=A)- and A is O or S, then L is        other than —C(═O)NR²— or —C(═S)NR²—.

Also of note are selected compounds of Formula I

-   -   Selection A. Compounds of Formula I wherein K is —NR¹C(=A)- and        A is O.    -   Selection B. Compounds of Formula I wherein L is —C(═B)NR²— and        B is O.    -   Selection C. Compounds of Selection B or Selection C wherein        -   J is a phenyl ring or a 5- or 6-membered heteroaromatic ring            selected from the group consisting of J-1, J-2, J-3 and J-4,            each J ring optionally substituted with 1 to 3 R⁵

-   -   -   Q is O, S or NR⁵;        -   W, X, Y and Z are independently N or CR⁵, provided that in            J-3 and J-4 at least one of W, X, Y or Z is N;        -   R¹ is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆            cycloalkyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl;        -   R² is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆            cycloalkyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl;        -   R³ is C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆            cycloalkyl each optionally substituted with one or more            substituents selected from the group consisting of halogen,            CN, C₁-C₂ alkoxy, C₁-C₂ alkylthio, C₁-C₂ alkylsulfinyl and            C₁-C₂ alkylsulfonyl;        -   one of the R⁴ groups is attached to the phenyl ring at the            2-position or 5-position, and said R⁴ is C₁-C₄ alkyl, C₁-C₄            haloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy,            C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl,            C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl or C₁-C₄            haloalkylsulfonyl;        -   each R⁵ is independently H, C₁-C₄ alkyl, C₁-C₄ haloalkyl,            halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄            alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄            haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄            haloalkylsulfonyl or C₂-C₄ alkoxycarbonyl, C₃-C₈            dialkylaminocarbonyl; or        -   each R⁵ is independently a phenyl, benzyl or a 5- or            6-membered heteroaromatic ring, each ring optionally            substituted with C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl,            C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄            haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄            alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄            alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈            dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆            (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆            alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈            dialkylaminocarbonyl or C₃-C₆ trialkylsilyl; or        -   (R⁵)₂ when attached to adjacent carbon atoms can be taken            together as —OCF₂O—, —CF₂CF₂O— or CF₂CF₂O—;        -   each R⁶ is independently C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆            alkynyl, optionally substituted with halogen, CN, C₁-C₄            alkoxy, C₁-C₄ alkylthio or R⁷; and        -   n is 1 to 2.

Of note are compounds of Selection C wherein K is —NR¹C(═O)— and L is—C(GR⁶)═N— or —SO₂NR²—. Also of note are compounds of Selection Cwherein L is —C(═O)NR²— and K is —N═C(GR⁶)— or —NR¹SO₂—.

-   -   Selection D. Compounds of Selection C wherein        -   R¹ is H or C₁-C₄ alkyl;        -   R² is H or C₁-C₄ alkyl;        -   R³ is C₁-C₄ alkyl optionally substituted with halogen, CN,            OCH₃, or S(O)_(p)CH₃;        -   one R⁵ group is attached to the J at the position ortho to            K, and said R⁵ is C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen, CN,            NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄            alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio,            C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl or C₂-C₄            alkoxycarbonyl; C₃-C₈ dialkylaminocarbonyl or a phenyl,            benzyl, or a 5- or 6-membered heteroaromatic ring, each ring            optionally substituted with halogen, CN, NO₂, C₁-C₄ alkyl,            C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄            haloalkyl, C₁-C₄ alkoxy or C₁-C₄ haloalkoxy;        -   and an optional second R⁵ group is independently C₁-C₄            alkyl, C₁-C₄ haloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy,            C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl,            C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄            haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl or C₂-C₄            alkoxycarbonyl; C₃-C₈ dialkylaminocarbonyl or a phenyl,            benzyl, or a 5- or 6-membered heteroaromatic ring, each ring            optionally substituted with halogen, CN, NO₂, C₁-C₄ alkyl,            C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄            haloalkyl, C₁-C₄ alkoxy or C₁-C₄ haloalkoxy;        -   G is O or S; and        -   p is 0, 1 or 2.    -   Selection E. Compounds of Selection D wherein J is phenyl,        pyrazole, pyrrole, pyridine or pyrimidine, each substituted with        one R⁵ attached to the J at the position ortho to K and a second        optional R⁵.    -   Selection F. Compounds of Selection L wherein        -   R¹ and R² are each H;        -   one R⁴ is attached at the 2-position ortho to the K-J moiety            and is selected from the group consisting of C₁-C₃ alkyl,            CF₃, OCF₃, OCHF₂, S(O)_(p)CF₃, S(O)_(p)CHF₂ and halogen and            an optional second R⁴ is attached at the 4-position para to            the K-J moiety and is selected from the group consisting of            halogen, C₁-C₃ alkyl and C₁-C₃ haloalkyl.    -   Selection G. Compounds of Selection F wherein        -   J is J-1;        -   Q is NR^(5a);        -   X is N or CH;        -   Y is CH; Z is CR^(5b);        -   R^(5a) is a phenyl or 2-pyridyl ring substituted with one or            two substituents selected from the group consisting of            halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl or C₁-C₄ haloalkoxy;            and        -   R^(5b) is halogen or CF₃.

One or more of the following methods and variations as described inSchemes 1-33 can be used to prepare the compounds of Formula I. Thedefinitions of A, B, J, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹ and n in thecompounds of Formulae 1-88 below are as defined above in the Summary ofthe Invention. Compounds of Formulae Ia-e, 2a-b, 4a-s, 5a-d are varioussubsets of the compounds of Formula I, 2, 4 and 5.

Compounds of Formula Ia (wherein K is NR¹C(═O)) can be prepared bycoupling of an amine of Formula 2 with an acid chloride of Formula 3 inthe presence of an acid scavenger to provide the compound of Formula Ia.Typical acid scavengers include amine bases such as triethylamine,diisopropylethylamine and pyridine; other scavengers include hydroxidessuch as sodium and potassium hydroxide and carbonates such as sodiumcarbonate and potassium carbonate. In certain instances it is useful touse polymer-supported acid scavengers such as polymer-bounddiisopropylethylamine and polymer-bound dimethylaminopyridine. Thecoupling can be run in a suitable inert solvent such as tetrahydrofuran,dioxane, diethylether or dichloromethane to afford the anilide ofFormula Ia. In a subsequent step, amides of Formula Ia can be convertedto thioamides of Formula Ib using a variety of standard thio transferreagents including phosphorus pentasulfide and Lawesson's reagent.

An alternate procedure for the preparation of compounds of Formula Iainvolves coupling of an amine of Formula 2 with an acid of Formula 4 inthe presence of a dehydrating agent such as dicyclohexylcarbodiimide(DCC). Polymer supported reagents are again useful here, such aspolymer-bound cyclohexylcarbodiimide. Synthetic procedures of Schemes 1and 2 are only representative examples of useful methods for thepreparation of Formula I compounds as the synthetic literature isextensive for this type of reaction.

One skilled in the art will also realize that acid chlorides of Formula3 may be prepared from acids of Formula 4 by numerous well-knownmethods. For example, acid chlorides of Formula 3 are readily made fromcarboxylic acids of Formula 4 by reacting the carboxylic acid 4 withthionyl chloride or oxalyl chloride in an inert solvent such as tolueneor dichloromethane in the presence of a catalytic amount ofN,N-dimethylformamide.

Amines of Formula 2a are typically available from the correspondingnitro compounds of Formula 5 via catalytic hydrogenation of the nitrogroup. Typical procedures involve reduction with hydrogen in thepresence of a metal catalyst such as palladium on carbon or platinumoxide and in hydroxylic solvents such as ethanol and isopropanol. Theycan also be prepared by reduction with zinc in acetic acid. Theseprocedures are well documented in the chemical literature. R¹substituents such as alkyl, substituted alkyl and the like can generallybe introduced at this stage through the generally preferred method ofreductive alkylation of the amine. A commonly employed procedure is tocombine the aniline 2a with an aldehyde in the presence of a reducingagent such as sodium cyanoborohydride to produce the Formula 2bcompounds where R¹ is alkyl, alkenyl, alkynyl or substituted derivativesthereof.

Compounds of Formula Ic (wherein K is N═C(GR⁶) can be prepared byreaction of imidoylhalides of Formula 6 with sulfur, oxygen and nitrogennucleophiles of Formula 7. Typically the reactions are conducted in thepresence of a base such as a tertiary amine or an alkali metalhydroxide.

Compounds of Formula 6 can be prepared from compounds of Formula Ia byreaction with an appropriate halogenating agent such as phosphorouspentachloride, phosphorous oxychloride, thionyl chloride or triphenylphosphine and carbon tetrachloride.

Alternatively compounds of Formula Id (wherein K is N═C(SR⁶)) when R⁶ isan alkyl or substituted alkyl group can be prepared from compounds ofFormula Ib by reaction with an alkyl halide of Formula 8 optionally inthe presence of a base such as a tertiary amine or an alkali metalalkoxide.

Compounds of Formula Ie (wherein K is NR¹SO₂) can be prepared byreacting an amine of Formula 2 with a sulfonyl chloride of Formula 9 inthe presence of an acid scavenger. Typical acid scavengers include aminebases such as triethylamine, diisopropylethylamine and pyridine; otherscavengers include hydroxides such as sodium and potassium hydroxide andcarbonates such as sodium carbonate and potassium carbonate. In certaininstances it is useful to use polymer-supported acid scavengers such aspolymer-bound diiospropylethylamine and polymer-bounddimethylaminopyridine.

Nitro compounds of Formula 5a (wherein L is C(═O)NR²) can be readilyprepared from commercially available 2-nitrobenzoic acids (Scheme 8).Typical methods for amide formation can be applied here. These includedirect dehydrative coupling of acids of Formula 10 with amines ofFormula 11 using for example DCC, and conversion of the acids to anactivated form such as the acid chlorides or anhydrides and subsequentcoupling with amines to form amides of Formula 5a. The chemicalliterature is extensive on this type of reaction. Amides of Formula 5aare readily converted to thioamides of Formula 5b by using commerciallyavailable thio transfer reagents such as phosphorus pentasulfide andLawesson's reagent.

Nitro compounds of Formula 5c (wherein L is C(GR⁶)═N) can be preparedfrom compounds of Formula 5a via imidoyl halides of Formula 12 bymethods similar to those described in Schemes 4 and 5.

Nitro compounds for Formula 5d (wherein L is SO₂NR²) can be preparedfrom amines of Formula 13 by diazotization with reagents such as sodiumnitrite or an alkyl nitrite and reaction with sulfur dioxide in thepresence of a copper catalyst (see for instance, Courtin, A. Helv. Chim.Acta, 1976, 59, 379-387) followed by reaction with amines of Formula 11(see Scheme 8). The synthesis of amines of Formula 13 is well known inthe art.

Benzoic acids of Formula 4a (compounds of Formula 4 wherein J is anoptionally substituted phenyl ring) are well known in the art.Preparation of certain heterocyclic acids of Formula 4 are described inSchemes 11-16. A variety of heterocyclic acids and general methods fortheir synthesis may be found in World Patent Application WO 98/57397.

The synthesis of representative pyridine acids (4b) is depicted inScheme 11. This procedure involves the known synthesis of pyridines fromβ-ketoesters and 4-aminobutenones (17). Substituent groups R⁵(c) andR⁵(d) include e.g. alkyl and haloalkyl.

The synthesis of representative pyrimidine acids (4c) is depicted inScheme 12. This procedure involves the known synthesis of pyrimidinesfrom vinylidene-β-ketoesters (20) and amidines. Substituent groups R⁵(c)and R⁵(d) include e.g. alkyl and haloalkyl.

Syntheses of representative pyrazole acids (4d-4g) are depicted inSchemes 13-16. The synthesis of 4d in Scheme 13 involves as the key stepintroduction of the R⁵(c) substituent via alkylation of the pyrazole.The alkylating agent R⁵(c)-Lg (wherein Lg is a leaving group such as Cl,Br, I, sulfonates such as p-toluenesulfonate or methanesulfonate orsulfates such as —SO₂OR⁵(c)) includes R⁵(c) groups such as C₁-C₆ alkyl,C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₆ halocycloalkyl, C₂-C₆alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₃-C₈ dialkylaminocarbonyl, C₃-C₆trialkylsilyl; or phenyl, benzyl, benzoyl, 5- or 6-memberedheteroaromatic ring or an aromatic 8-, 9- or 10-membered fusedheterobicyclic ring system, each ring or ring system optionallysubstituted. Oxidation of the methyl group affords the pyrazolecarboxylic acid. Some of the more preferred R⁵(d) groups includehaloalkyl.

Some pyrazole acids of Formula 4d may be prepared via metallation andcarboxylation of pyrazoles of Formula 26 as the key step (Scheme 14).The R⁵(c) group is introduced in a manner similar to that of Scheme 13,i.e. via alkylation with a R⁵(c) alkylating agent. Representative R⁵(d)groups include e.g. cyano and haloalkyl.

This procedure is particularly useful for preparing1-(2-pyridinyl)pyrazolecarboxylic acids of Formula 4e, related topreferred moiety J-5 wherein R⁵ is a substituted 2-pyridinyl ring, asshown in Scheme 15. Reaction of a pyrazole of Formula 27 with a2,3-dihalopyridine of Formula 23 affords good yields of the1-pyridinylpyrazole of Formula 28 with good specificity for the desiredregiochemistry. Metallation of 28 with lithium diisopropylamide (LDA)followed by quenching of the lithium salt with carbon dioxide affordsthe 1-(2-pyridinyl)pyrazolecarboxylic acid of Formula 4e.

Other pyrazoles of Formula 4d can be prepared via reaction of anoptionally substituted phenyl hydrazine of Formula 30 with a pyruvate ofFormula 29 to yield pyrazole esters of Formula 31 (Scheme 16).Hydrolysis of the ester affords the pyrazole acids 4d. This procedure isparticularly useful for the preparation of compounds where R⁵(c) isoptionally substituted phenyl and R⁵(d) is haloalkyl.

Pyrazole acids of Formula 4d can also be prepared via 3+2 cycloadditionof an appropriately substituted nitrilimine of Formula 32 with eithersubstituted propiolates of Formula 33 or acrylates of Formula 34 (Scheme17). Cycloaddition with acrylates requires additional oxidation of theintermediate pyrazoline to the pyrazole. Hydrolysis of the ester ofFormula 31 affords the pyrazole acids 4d. Preferred iminohalides forthis reaction include the trifluoromethyl iminochloride (35) and theiminodibromide (36). Compounds such as 35 are known (J. Heterocycl.Chem. 1985, 22(2), 565-8). Compounds such as 36 are available by knownmethods (Tetrahedron Letters 1999, 40, 2605). These procedures areparticularly useful for the preparation of compounds where R⁵(c) isoptionally substituted phenyl and R⁵(d) is haloalkyl or bromo.

The starting pyrazoles of Formula 25 are known compounds or can beprepared according to known methods. The pyrazole of Formula 25a (thecompound of Formula 25 wherein R⁵(d) is CF₃) can be prepared byliterature procedures (J. Fluorine Chem. 1991, 53(1), 61-70). Thepyrazoles of Formula 25b (compounds of Formula 25 wherein R⁵(d) is Cl orBr) can be prepared by literature procedures (Chem. Ber. 1966, 99(10),33507). A useful alternative method for the preparation of compound 25bis depicted in Scheme 18. Metallation of the sulfamoyl pyrazole ofFormula 37 with n-butyllithium followed by direct halogenation of theanion with either hexachloroethane (for R⁵(d) being Cl) or1,2-dibromotetrachloroethane (for R⁵(d) being Br) affords thehalogenated derivatives of Formula 38a. Removal of the sulfamoyl groupwith trifluoroacetic acid (TFA) at room temperature proceeds cleanly andin good yield to afford the pyrazoles of Formula 25c. One skilled in theart will recognize that Formula 25c is a tautomer of Formula 25b.

Pyrazolecarboxylic acids of Formula 4f wherein R¹⁰ is CF₃ can beprepared by the method outlined in Scheme 19.

Reaction of a compound of Formula 38b wherein R¹² is C₁-C₄ alkyl with asuitable base in a suitable organic solvent affords the cyclized productof Formula 39 after neutralization with an acid such as acetic acid. Thesuitable base can be, for example but not limitation, sodium hydride,potassium t-butoxide, dimsyl sodium (CH₃S(O)CH₂ ⁻Na⁺), alkali metal(such as lithium, sodium or potassium) carbonates or hydroxides,tetraalkyl (such as methyl, ethyl or butyl)ammonium fluorides orhydroxides, or2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphonine.The suitable organic solvent can be, for example but not limitation,acetone, acetonitrile, tetrahydrofuran, dichloromethane,dimethylsulfoxide, or N,N-dimethylformamide. The cyclization reaction isusually conducted in a temperature range from about 0 to 120° C. Theeffects of solvent, base, temperature and addition time are allinterdependent, and choice of reaction conditions is important tominimize the formation of byproducts. A preferred base istetrabutylammonium fluoride.

Dehydration of the compound of Formula 39 to give the compound ofFormula 40, followed by converting the carboxylic ester function tocarboxylic acid, affords the compound of Formula 4f. The dehydration iseffected by treatment with a catalytic amount of a suitable acid. Thiscatalytic acid can be, for example but not limitation, sulfuric acid.The reaction is generally conducted using an organic solvent. As oneskilled in the art will realize, dehydration reactions may be conductedin a wide variety of solvents in a temperature range generally betweenabout 0 and 200° C., more preferably between about 0 and 100° C.). Forthe dehydration in the method of Scheme 19, a solvent comprising aceticacid and temperatures of about 65° C. are preferred. Carboxylic estercompounds can be converted to carboxylic acid compounds by numerousmethods including nucleophilic cleavage under anhydrous conditions orhydrolytic methods involving the use of either acids or bases (see T. W.Greene and P. G. M. Wuts, Protective Groups in Organic Synthesis, 2nded., John Wiley & Sons, Inc., New York, 1991, pp. 224-269 for a reviewof methods). For the method of Scheme 19, base-catalyzed hydrolyticmethods are preferred. Suitable bases include alkali metal (such aslithium, sodium or potassium) hydroxides. For example, the ester can bedissolved in a mixture of water and an alcohol such as ethanol. Upontreatment with sodium hydroxide or potassium hydroxide, the ester issaponified to provide the sodium or potassium salt of the carboxylicacid. Acidification with a strong acid, such as hydrochloric acid orsulfuric acid, yields the carboxylic acid of Formula 4f. The carboxylicacid can be isolated by methods known to those skilled in the art,including crystallization, extraction and distillation.

Compounds of Formula 38b can be prepared by the method outlined inScheme 20.

Treatment of a hydrazine compound of Formula 41 with a ketone of Formula42 in a solvent such as water, methanol or acetic acid gives thehydrazone of Formula 43. One skilled in the art will recognize that thisreaction may require catalysis by an optional acid and may also requireelevated temperatures depending on the molecular substitution pattern ofthe hydrazone of Formula 43. Reaction of the hydrazone of Formula 43with the compound of Formula 44 in a suitable organic solvent such as,for example but not limitation, dichloromethane or tetrahydrofuran inthe presence of an acid scavenger such as triethylamine provides thecompound of Formula 38. The reaction is usually conducted at atemperature between about 0 and 100° C. Hydrazine compounds of Formula98 can be prepared by standard methods, such as by contacting thecorresponding halo compound of Formula 23 (Scheme 15) with hydrazine.

Pyrazolecarboxylic acids of Formula 4g wherein R¹⁰ is Cl or Br can beprepared by the method outlined in Scheme 21.

Oxidization of the compound of Formula 45 optionally in the presence ofacid to give the compound of Formula 46 followed by conversion of thecarboxylic ester function to the carboxylic acid provides the compoundof Formula 4g. The oxidizing agent can be hydrogen peroxide, organicperoxides, potassium persulfate, sodium persulfate, ammonium persulfate,potassium monopersulfate (e.g., Oxone®) or potassium permanganate. Toobtain complete conversion, at least one equivalent of oxidizing agentversus the compound of Formula 45 should be used, preferably betweenabout one to two equivalents. This oxidation is typically carried out inthe presence of a solvent. The solvent can be an ether, such astetrahydrofuran, p-dioxane and the like, an organic ester, such as ethylacetate, dimethyl carbonate and the like, or a polar aprotic organicsuch as N,N-dimethylformamide, acetonitrile and the like. Acids suitablefor use in the oxidation step include inorganic acids, such as sulfuricacid, phosphoric acid and the like, and organic acids, such as aceticacid, benzoic acid and the like. The acid, when used, should be used ingreater than 0.1 equivalents versus the compound of Formula 45. Toobtain complete conversion, one to five equivalents of acid can be used.The preferred oxidant is potassium persulfate and the oxidation ispreferably carried out in the presence of sulfuric acid. The reactioncan be carried out by mixing the compound of Formula 45 in the desiredsolvent and, if used, the acid. The oxidant can then be added at aconvenient rate. The reaction temperature is typically varied from aslow as about 0° C. up to the boiling point of the solvent in order toobtain a reasonable reaction time to complete the reaction, preferablyless than 8 hours. The desired product, a compound of Formula 46, can beisolated by methods known to those skilled in the art, includingcrystallization, extraction and distillation. Methods suitable forconverting the ester of Formula 46 to the carboxylic acid of Formula 4gare already described for Scheme 19.

Compounds of Formula 45 can be prepared from corresponding compounds ofFormula 47 as shown in Scheme 22.

Treatment of a compound of Formula 47 with a halogenating reagent,usually in the presence of a solvent, affords the corresponding halocompound of Formula 45. Halogenating reagents that can be used includephosphorus oxyhalides, phosphorus trihalides, phosphorus pentahalides,thionyl chloride, dihalotlialkylphophoranes, dihalodiphenylphosphoranes,oxalyl chloride and phosgene. Preferred are phosphorus oxyhalides andphosphorus pentalhalides. To obtain complete conversion, at least 0.33equivalents of phosphorus oxyhalide versus the compound of Formula 47should be used, preferably between about 0.33 and 1.2 equivalents. Toobtain complete conversion, at least 0.20 equivalents of phosphoruspentahalide versus the compound of Formula 47 should be used, preferablybetween about 0.20 and 1.0 equivalents. Compounds of Formula 47 whereinR¹³ is C₁-C₄ alkyl are preferred for this reaction. Typical solvents forthis halogenation include halogenated alkanes, such as dichloromethane,chloroform, chlorobutane and the like, aromatic solvents, such asbenzene, xylene, chlorobenzene and the like, ethers, such astetrahydrofuran, p-dioxane, diethyl ether, and the like, and polaraprotic solvents such as acetonitrile, N,N-dimethylformamide, and thelike. Optionally, an organic base, such as triethylamine, pyridine,N,N-dimethylaniline or the like, can be added. Addition of a catalyst,such as N,N-dimethylformamide, is also an option. Preferred is theprocess in which the solvent is acetonitrile and a base is absent.Typically, neither a base nor a catalyst is required when acetonitrilesolvent is used. The preferred process is conducted by mixing thecompound of Formula 47 in acetonitrile. The halogenating reagent is thenadded over a convenient time, and the mixture is then held at thedesired temperature until the reaction is complete. The reactiontemperature is typically between 20° C. and the boiling point ofacetonitrile, and the reaction time is typically less than 2 hours. Thereaction mass is then neutralized with an inorganic base, such as sodiumbicarbonate, sodium hydroxide and the like, or an organic base, such assodium acetate. The desired product, a compound of Formula 45, can beisolated by methods known to those skilled in the art, includingcrystallization, extraction and distillation.

Alternatively, compounds of Formula 45 wherein R¹⁰ is Br or Cl can beprepared by treating the corresponding compounds of Formula 45 whereinR¹⁰ is a different halogen (e.g., Cl for making Formula 45 wherein R¹⁰is Br) or a sulfonate group such as p-toluenesulfonate with hydrogenbromide or hydrogen chloride, respectively. By this method the R¹⁰halogen or sulfonate substituent on the Formula 45 starting compound isreplaced with Br or Cl from hydrogen bromide or hydrogen chloride,respectively. The reaction is conducted in a suitable solvent such asdibromomethane, dichloromethane or acetonitrile. The reaction can beconducted at or near atmospheric pressure or above atmospheric pressurein a pressure vessel. When R¹⁰ in the starting compound of Formula 45 isa halogen such as Cl, the reaction is preferably conducted in such a waythat the hydrogen halide generated from the reaction is removed bysparging or other suitable means. The reaction can be conducted betweenabout 0 and 100° C., most conveniently near ambient temperature (e.g.,about 10 to 40° C.), and more preferably between about 20 and 30° C.Addition of a Lewis acid catalyst (such as aluminum tribromide forpreparing Formula 45 wherein R¹⁰ is Br) can facilitate the reaction. Theproduct of Formula 45 is isolated by the usual methods known to thoseskilled in the art, including extraction, distillation andcrystallization.

Starting compounds of Formula 45 wherein R¹⁰ is Cl or Br can be preparedfrom corresponding compounds of Formula 47 as already described.Starting compounds of Formula 45 wherein R¹⁰ is a sulfonate group canlikewise be prepared from corresponding compounds of Formula 47 bystandard methods such as treatment with a sulfonyl chloride (e.g.,p-toluenesulfonyl chloride) and base such as a tertiary amine (e.g.,triethylamine) in a suitable solvent such as dichloromethane.

Pyrazolecarboxylic acids of Formula 4h wherein R¹⁰ is OCH₂CF₃ can beprepared by the method outlined in Scheme 23. In this method, instead ofbeing halogenated as shown in Scheme 22, the compound of Formula 47 isoxidized to the compound of Formula 48. The reaction conditions for thisoxidation are as already described for the conversion of the compound ofFormula 45 to the compound of Formula 46 in Scheme 21.

The compound of Formula 48 is then alkylated to form the compound ofFormula 50 by contact with an alkylating agent CF₃CH₂Lg (49) in thepresence of a base. In the alkylating agent 49, Lg is a nucleophilicreaction leaving group such as halogen (e.g., Br, I), OS(O)₂CH₃(methanesulfonate), OS(O)₂CF₃, OS(O)₂Ph-p-CH₃ (p-toluenesulfonate), andthe like; methanesulfonate works well. The reaction is conducted in thepresence of at least one equivalent of a base. Suitable bases includeinorganic bases, such as alkali metal (such as lithium, sodium orpotassium) carbonates and hydroxides, and organic bases, such astriethylamine, diisopropylethylamine and1,8-diazabicyclo[5.4.0]undec-7-ene. The reaction is generally conductedin a solvent, which can comprise alcohols, such as methanol and ethanol,halogenated alkanes, such as dichloromethane, aromatic solvents, such asbenzene, toluene and chlorobenzene, ethers, such as tetrahydrofuran, andpolar aprotic solvents, such as acetonitrile, N,N-dimethylformamide, andthe like. Alcohols and polar aprotic solvents are preferred for use withinorganic bases. Potassium carbonate as base and acetonitrile as solventare preferred. The reaction is generally conducted between about 0 and150° C., with most typically between ambient temperature and 100° C. Theproduct of Formula 50 can be isolated by conventional techniques such asextraction. The ester of Formula 50 can then be converted to thecarboxylic acid of Formula 4h by the methods already described for theconversion of Formula 40 to Formula 4f in Scheme 19.

Compounds of Formula 47 can be prepared from compounds of Formula 41(Scheme 20) as outlined in Scheme 24.

In this method, a hydrazine compound of Formula 41 is contacted with acompound of Formula 51 (a fumarate ester or maleate ester or a mixturethereof may be used) in the presence of a base and a solvent. The baseis typically a metal alkoxide salt, such as sodium methoxide, potassiummethoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide,lithium tert-butoxide, and the like. Greater than 0.5 equivalents ofbase versus the compound of Formula 51 should be used, preferablybetween 0.9 and 1.3 equivalents. Greater than 1.0 equivalents of thecompound of Formula 108 should be used, preferably between 1.0 to 1.3equivalents. Polar protic and polar aprotic organic solvents can beused, such as alcohols, acetonitrile, tetrahydrofuran,N,N-dimethylformamide, dimethyl sulfoxide and the like. Preferredsolvents are alcohols such as methanol and ethanol. It is especiallypreferred that the alcohol be the same as that making up the fumarate ormaleate ester and the alkoxide base. The reaction is typically conductedby mixing the compound of Formula 108 and the base in the solvent. Themixture can be heated or cooled to a desired temperature and thecompound of Formula 98 added over a period of time. Typically reactiontemperatures are between 0° C. and the boiling point of the solventused. The reaction may be conducted under greater than atmosphericpressure in order to increase the boiling point of the solvent.Temperatures between about 30 and 90° C. are generally preferred. Theaddition time can be as quick as heat transfer allows. Typical additiontimes are between 1 minute and 2 hours. Optimum reaction temperature andaddition time vary depending upon the identities of the compounds ofFormula 98 and Formula 51. After addition, the reaction mixture can beheld for a time at the reaction temperature. Depending upon the reactiontemperature, the required hold time may be from 0 to 2 hours. Typicalhold times are 10 to 60 minutes. The reaction mass then can be acidifiedby adding an organic acid, such as acetic acid and the like, or aninorganic acid, such as hydrochloric acid, sulfuric acid and the like.Depending on the reaction conditions and the means of isolation, the—CO₂R¹³ function on the compound of Formula 47 may be hydrolyzed to—CO₂H; for example, the presence of water in the reaction mixture canpromote such hydrolysis. If the carboxylic acid (—CO₂H) is formed, itcan be converted back to —CO₂R¹³ wherein R¹³ is C₁-C₄ alkyl usingesterification methods well-known in the art. The desired product, acompound of Formula 47, can be isolated by methods known to thoseskilled in the art, such as crystallization, extraction or distillation.

The synthesis of representative pyrazole acids of Formula 4i is depictedin Scheme 25. Reaction of a dimethylaminoylidene ketoester of Formula 53with substituted hydrazines of formula 30 affords the pyrazoles ofFormula 54. Preferred R⁵(c) substituents include alkyl and haloalkyl,with 2,2,2-trifluoroethyl especially preferred. The esters of Formula 54are converted to the acids of Formula 4i by standard hydrolysis.

The synthesis of pyrazole acids of Formula 4j, which are related to thepreferred moiety J-6 wherein R⁵ is a substituted 2-pyridyl moietyattached to the 5-position of the pyrazole ring, is depicted in Scheme26. This synthesis is conducted according to the general synthesisdescribed in Scheme 27.

The synthesis of representative pyrazole acids of Formula 4k, as well asan alternative synthesis of Formula 4i, is depicted in Scheme 27.Reaction of the dimethylaminoylidene ketoester of Formula 53 withhydrazine affords the pyrazole of Formula 59. Reaction of the pyrazole59 with alkylating agents of Formula 60 (R⁵(c)-Lg wherein Lg is aleaving group such as halogen (e.g., Br, I), OS(O)₂CH₃(methanesulfonate), OS(O)₂CF₃, OS(O)₂Ph-p-CH₃ (p-toluenesulfonate), andthe like) affords a mixture of pyrazoles of Formulae 61 and 62. Thismixture of pyrazole isomers is readily separated by chromatographicmethods and converted to the corresponding acids. Preferred R⁵(c)substituents include alkyl and haloalkyl groups.

Of note is the synthesis of pyridinylpyrazole acids of Formula 4m, whichare related to Formula J-7 wherein R⁵ is a substituted 2-pyridinyl andattached to the 3-position of the pyrazole ring, as well as analternative synthesis of Formula 4j, is depicted in Scheme 28. Thissynthesis is conducted according to the general synthesis described inScheme 27.

A general synthesis of pyrrole acids of Formula 4n is depicted in Scheme29. Treatment of a compound of Formula 67 with2,5-dimethoxytetrahydrofuran (68) affords a pyrrole of Formula 69.Formylation of the pyrrole 69 to provide the aldehyde of Formula 70 canbe accomplished by using standard Vilsmeier-Haack formylationconditions, such as N,N-dimethylformamide (DMF) and phosphorusoxychloride. Halogenation of the compound of Formula 70 withN-halosuccinimides (NXS) such as N-chlorosuccinimide orN-bromosuccinimide occurs preferentially at the 4-position of thepyrrole ring. Oxidation of the halogenated aldehyde affords the pyrroleacid of Formula 4n. The oxidation can be accomplished by using a varietyof standard oxidation conditions.

The synthesis of certain pyridinylpyrrole acids of Formula 4o, which arerelated to Formula J-8 wherein R⁵ is 2-pyridinyl and attached to thenitrogen of the pyrrole ring, is depicted in Scheme 30. The compound ofFormula 72, 3-chloro-2-aminopyridine, is a known compound (see J.Heterocycl. Chem. 1987, 24(5), 1313-16). A convenient preparation of 72from the 2-aminopyridine of Formula 71 involves protection,ortho-metallation, chlorination and subsequent deprotection. Theremaining synthesis is conducted according to the general synthesisdescribed in Scheme 29.

The synthesis of pyrrole acids of Formula 4p is depicted in Scheme 31.Cycloaddition of an allene of Formula 78 with a phenylsulfonyl hydrazideof Formula 77 (see Pavri, N. P.; Trudell, M. L. J. Org. Chem. 1997, 62,2649-2651) affords a pyrroline of Formula 79. Treatment of the pyrrolineof Formula 79 with tetrabutylammonium fluoride (TBAF) gives a pyrrole ofFormula 80. Reaction of the pyrrole 80 with an alkylating agent R⁵(d)-Lg(wherein Lg is a leaving group as defined above), followed byhydrolysis, affords a pyrrole acid of Formula 4p.

The synthesis of pyrrole acids of Formula 4q, which are related toFormula J-9 wherein R⁵ is phenyl or 2-pyridyl and attached to the2-position of the pyrrole ring, is depicted in Scheme 32. The synthesisis conducted according to the general method described for Scheme 31.

The synthesis of pyrrole acids of Formula 4r is depicted in Scheme 33.Reaction of an α,β-unsaturated ester of Formula 85 withp-tolylsulfonylmethyl isocyanide (TosMIC) provides a pyrrole of Formula86. For a leading reference, see Xu, Z. et al, J. Org. Chem., 1988, 63,5031-5041. Reaction of the pyrrole of Formula 86 with an alkylatingagent R⁵(d)-Lg (wherein Lg is a leaving group as defined above) followedby hydrolysis affords a pyrrole acid of Formula 4r.

The synthesis of pyrrole acids of Formula 4s, which are related toFormula J-6, wherein R⁵ is a substituted phenyl or a substituted2-pyridinyl ring, is depicted in Scheme 35. The synthesis is conductedaccording to the general method described for Scheme 33.

It is recognized that some reagents and reaction conditions describedabove for preparing compounds of Formula I may not be compatible withcertain functionalities present in the intermediates. In theseinstances, the incorporation of protection/deprotection sequences orfunctional group interconversions into the synthesis will aid inobtaining the desired products. The use and choice of the protectinggroups will be apparent to one skilled in chemical synthesis (see, forexample, Greene, T. W.; Wuts, P. G. M. Protective Groups in OrganicSynthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art willrecognize that, in some cases, after the introduction of a given reagentas it is depicted in any individual scheme, it may be necessary toperform additional routine synthetic steps not described in detail tocomplete the synthesis of compounds of Formula 1. One skilled in the artwill also recognize that it may be necessary to perform a combination ofthe steps illustrated in the above schemes in an order other than thatimplied by the particular sequence presented to prepare the compounds ofFormula 1.

One skilled in the art will also recognize that compounds of Formula 1and the intermediates described herein can be subjected to variouselectrophilic, nucleophilic, radical, organometallic, oxidation, andreduction reactions to add substituents or modify existing substituents.

Without further elaboration, it is believed that one skilled in the artusing the preceding description can utilize the present invention to itsfullest extent. The following Examples are, therefore, to be construedas merely illustrative, and not limiting of the disclosure in any waywhatsoever. Percentages are by weight except for chromatographic solventmixtures or where otherwise indicated. Parts and percentages forchromatographic solvent mixtures are by volume unless otherwiseindicated. ¹H NMR spectra are reported in ppm downfield fromtetramethylsilane; s means singlet, d means doublet, t means triplet, qmeans quartet, m means multiplet, dd means doublet of doublets, dt meansdoublet of triplets, br s means broad singlet and br d means broaddoublet.

EXAMPLE 1 Preparation ofN-[2-methyl-6-[[(1-methylethyl)amino]sulfonyl]phenyl]-4-(trifluoromethoxy)benzamideStep A: Preparation of3-methyl-N-(1-methylethyl)-2-nitrobenzenesulfonamide

To a solution of isopropylamine (13 mL, 155 mmol) in 60 mL ofdichloromethane at 0° C. was added a solution of 5.3 g of3-methyl-2-nitrobenzenesulfonyl chloride (prepared according to Courtin,A. Helv. Chim. Acta, 1976, 59, 379-387) in 60 mL of dichloromethanedropwise. The reaction mixture was stirred 2 hours at room temperature.Water was added and the layers were separated. The organic layer wasdried (sodium sulfate) and the volatiles were removed with a rotaryevaporator. The residue was purified by medium pressure liquidchromatography (MPLC), using 20-40% ethyl acetate in hexanes as eluant,to afford 4.3 g of the title compound as a yellow solid.

¹H NMR (CDCl₃) δ 1.12 (d, 6H), 2.39 (s, 1H), 3.56 (m, 1H), 4.65 (br d,1H), 7.54 (m, 2H), 7.91 (dd, 1H).

Step B: Preparation of2-amino-3-methyl-N-(1-methylethyl)benzenesulfonamide

To a mixture of 4.13 g of the material from Step A and 0.25 g of 10%palladium on carbon was added 150 mL of ethanol. The reaction mixturewas stirred under a balloon of hydrogen for three days. The mixture wasfiltered through celite and the solvent was removed with a rotaryevaporator to afford 3.65 g of the title compound as a brown oil.

¹H NMR (CDCl₃) δ 1.03 (d, 6H), 2.21 (s, 1H), 3.60 (m, 1H), 4.57 (br d,1H), 4.86 (br s, 2H), 6.73 (dd, 1H), 7.24 (d, 1H), 7.64 (d, 1H).

Step C: Preparation ofN-[2-methyl-6-[[(1-methylethyl)amino]sulfonyl]phenyl]-4-(trifluoromethoxy)benzamide

To 0.30 g (1.4 mmol) of the material from Step B in 5 mL of chloroformwas added 0.28 ml (3.5 mmol) of pyridine and 0.27 mL (1.7 mmol) of4-(trifluoromethoxy)benzoyl chloride. The reaction mixture was stirredovernight at room temperature and then heated at reflux for 5 hours.After cooling to room temperature the reaction mixture was washed with1N HCl, dried (sodium sulfate) and filtered. The volatiles were removedwith a rotary evaporator. The residue was purified by MPLC (5-25% ethylacetate in hexanes as eluant) to afford 0.10 g of the title compound, acompound of the invention, as a white solid melting at 104-107° C.

¹H NMR (CDCl₃) δ 0.99 (d, 6H), 2.36 (s, 1H), 3.32 (m, 1H), 4.07 (br d,1H), 7.35 (m, 3H), 7.56 (d, 1H), 7.89 (d, 1H), 8.05 (d, 2H), 8.78 (br s,1H).

EXAMPLE 2 Preparation of2-[[[1-(3-Chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]sulfonyl]amino]-3-methyl-N-(1-methylethyl)benzamideStep A: Preparation of3-chloro-2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyridine

To a mixture of 2,3-dichloropyridine (99.0 g, 0.67 mol) and3-trifluoromethyl pyrazole (83 g, 0.61 mol) in dry N,N-dimethylformamide(300 mL) was added potassium carbonate (166.0 g, 1.2 mol) and thereaction was then heated to 110-125° C. over 48 hours. The reaction wascooled to 100° C. and filtered through Celite® diatomaceous filter aidto remove solids. N,N-Dimethylformamide and excess dichloropyridine wereremoved by distillation at atmospheric pressure. Distillation of theproduct at reduced pressure (b.p. 139-141° C., 7 mm) afforded thedesired intermediate as a clear yellow oil (113.4 g).

¹H NMR (CDCl₃) δ 6.78 (s, 1H), 7.36 (t, 1H), 7.93 (d, 1H), 8.15 (s, 1H),8.45 (d, 1H).

Step B: Preparation of Lithium1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-sulfinate

To a solution of isopropylamine (2.5 mL, 30 mmol) in 25 mL oftetrahydrofuran at −78° C. was added dropwise 7.1 mL (18 mmol) of a 2.5Msolution of n-butyllithium in hexanes. This solution was added viacannula to a solution of 4.0 g of3-chloro-2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyridine (i.e. the titlematerial from Step A) in 50 mL of tetrahydrofuran at −78° C. Thereaction mixture turned orange. After 15 minutes an additional 20 mL oftetrahydrofuran was added. Sulfur dioxide was bubbled through thesolution for 5 minutes. The orange color disappeared. After 15 minutesthe reaction mixture was filtered and the solvent was removed from thefiltrate with a rotary evaporator. The residue was triturated with etherto afford 4.53 g of the title compound as an off-white solid.

1H NMR (D₂O) δ 7.08 (s, 1H), 7.72 (dd, 1h), 8.24 (dd, 1h), 8.55 (dd,1h).

Step C: Preparation of1-(3-Chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-sulfonic acid

To 100 mL of pH 6 buffer (prepared by dissolving 1.2 g (10 mmol) ofsodium dihydrogenphosphate in 100 mL of water and adding 11.2 mL of 1Nsodium hydroxide) was added 3.52 g (11.1 mmol) of the title materialfrom Step B. This solution was cooled in an ice bath and 75 mL of ethylacetate and 1.48 g (11.1 mmol) of N-chlorosuccinimide were added. After30 minutes the layers were separated. The organic layer was dried(sodium sulfate) and the solvent was removed with a rotary evaporator.To the residue was added carbon tetrachloride and the solids wereremoved by filtration. The solvent was removed from the filtrate with arotary evaporator to afford 2.84 g of the title compound as an amberoil. ¹HNMR(CDCl₃) δ 7.45 (s, 1H), 7.58 (dd, 1h), 8.01 (dd, 1h), 8.58(dd, 1h).

Step D: Preparation of 3-methyl-N-(1-methylethyl)-2-nitrobenzamide

A solution of 3-methyl-2-nitrobenzoic acid (2.00 g, 11.0 mmol) andtriethylamine (1.22 g, 12.1 mmol) in 25 mL of dichloromethane was cooledto 10° C. Ethyl chloroformate was carefully added and a solidprecipitate formed. After the mixture was stirred for 30 minutesisopropylamine (0.94 g, 16.0 mmol) was added and a homogeneous solutionresulted. The reaction mixture was stirred for an additional hour,poured into water and extracted with ethyl acetate. The organic extractswere washed with water, dried over magnesium sulfate and evaporatedunder reduced pressure to afford 1.96 g of the desired intermediate as awhite solid melting at 126-128° C.

¹H NMR (CDCl₃) δ 1.24 (d, 6H), 2.38 (s, 3H), 4.22 (m, 1H), 5.80 (br s,1H), 7.4 (m, 3H).

Step E: Preparation of 2-amino-3-methyl-N-(1-methylethyl)benzamide

The 2-nitrobenzamide of Step D (1.70 g, 7.6 mmol) was hydrogenated over5% palladium on carbon in 40 mL of ethanol at 345 kPa (50 psi). When theuptake of hydrogen ceased the reaction was filtered through Celite®filter agent and the Celite® was washed with ether. The filtrate wasevaporated under reduced pressure to afford 1.41 g of the title compoundas a solid melting at 149-151° C.

¹H NMR (CDCl₃) δ 1.24 (dd, 6H), 2.16 (s, 3H), 4.25 (m, 1H), 5.54 (br s,2H), 5.85 (br s, 1H), 6.59 (t, 1H), 7.13 (d, 1H), 7.17 (d, 1H).

Step F: Preparation of2-[[[1-(3-Chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]sulfonyl]amino]-3-methyl-N-(1-methylethyl)benzamide

To 2.84 g (10.2 mmol) of1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-sulfonic acid(i.e. the title material from Step C) in 70 mL of dichloromethane wasadded 1.96 g (10.2 mmol) of 2-amino-3-methyl-N-(1-methylethyl)benzamide(i.e. the title compound of Step E) 1.78 mL (10.2 mmol) ofdiisopropylethylamine and approximately 5 mg of4-(dimethylamino)pyridine. The reaction mixture was stirred for 9 hours,then washed with water and dried (sodium sulfate). The solvent wasremoved with a rotary evaporator. The residue was purified by MPLC(20-40% ethyl acetate in hexanes as eluant) to afford 0.50 g of thetitle compound as a foamy white solid melting at 69-72° C.

¹H NMR (CDCl₃) δ 0.1.12 (d, 6H), 2.32 (s, 1H), 3.85 (m, 1H), 5.96 (brd,1H), 7.07 (s, 1H), 7.35 (m, 3H), 7.39 (dd, 1H), 7.89 (dd, 1H), 8.20 (dd,1H), 9.26 (s, 1H).

EXAMPLE 3 Preparation of3-Bromo-1-(3-chloro-2-pyridinyl)-N-[2-methyl-6-(3-methyl-1-oxobutyl)phenyl]-1H-pyrazole-5-carboxamideStep A: Preparation of 3-bromo-N,N-dimethyl-1H-pyrazole-1-sulfonamide

To a solution of N,N-dimethylsulfamoylpyrazole (44.0 g, 0.251 mol) indry tetrahydrofuran (500 mL) at −78° C. was added dropwise a solution ofn-butyllithium (2.5 M in hexane, 105.5 mL, 0.264 mol) while maintainingthe temperature below −60° C. A thick solid formed during the addition.Upon completion of the addition the reaction mixture was maintained foran additional 15 minutes, after which time a solution of1,2-dibromo-tetrachloroethane (90 g, 0.276 mol) in tetrahydrofuran (150mL) was added dropwise while maintaining the temperature below −70° C.The reaction mixture turned a clear orange; stirring was continued foran additional 15 minutes. The −78° C. bath was removed and the reactionwas quenched with water (600 mL). The reaction mixture was extractedwith dichloromethane (4×), and the organic extracts were dried overmagnesium sulfate and concentrated. The crude product was furtherpurified by chromatography on silica gel using dichloromethane-hexane(50:50) as eluent to afford the title compound as a clear colorless oil(57.04 g).

¹H NMR (CDCl₃) δ 3.07 (d, 6H), 6.44 (m, 1H), 7.62 (m, 1H).

Step B: Preparation of 3-bromopyrazole

To trifluoroacetic acid (70 mL) was slowly added3-bromo-N,N-dimethyl-1H-pyrazole-1-sulfonamide (i.e. the bromopyrazoleproduct of Step A) (57.04 g). The reaction mixture was stirred at roomtemperature for 30 minutes and then concentrated at reduced pressure.The residue was taken up in hexane, insoluble solids were filtered off,and the hexane was evaporated to afford the crude product as an oil. Thecrude product was further purified by chromatography on silica gel usingethyl acetate/dichloromethane (10:90) as eluent to afford an oil. Theoil was taken up in dichloromethane, neutralized with aqueous sodiumbicarbonate solution, extracted with dichloromethane (3×), dried overmagnesium sulfate and concentrated to afford the title compound as awhite solid (25.9 g), m.p. 61-64° C.

¹H NMR (CDCl₃) δ 6.37 (d, 1H), 7.59 (d, 1H), 12.4 (br s, 1H).

Step C: Preparation of 2-(3-bromo-1H-pyrazol-1-yl)-3-chloropyridine

To a mixture of 2,3-dichloropyridine (27.4 g, 185 mmol) and3-bromopyrazole (i.e. the product of Step B) (25.4 g, 176 mmol) in dryN,N-dimethylformamide (88 mL) was added potassium carbonate (48.6 g, 352mmol), and the reaction mixture was heated to 125° C. for 18 hours. Thereaction mixture was cooled to room temperature and poured into icewater (800 mL). A precipitate formed. The aqueous mixture ofprecipitated solids was stirred for 1.5 hours, filtered and washed withwater (2×100 mL). The solid filter cake was taken up in dichloromethaneand washed sequentially with water, 1N hydrochloric acid, saturatedaqueous sodium bicarbonate solution, and brine. The organic extractswere then dried over magnesium sulfate and concentrated to afford 39.9 gof a pink solid. The crude solid was suspended in hexane and stirredvigorously for 1 hour. The solids were filtered, washed with hexane anddried to afford the title compound as an off-white powder (30.4 g)determined to be >94% pure by NMR. This material was used withoutfurther purification in Step D.

¹H NMR (CDCl₃) δ 6.52 (s, 1H), 7.30 (dd, 1H), 7.92 (d, 1H), 8.05 (s,1H), 8.43 (d, 1H).

Step D: Preparation of3-Bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxylic acid

To a solution of 2-(3-bromo-1H-pyrazol-1-yl)-3-chloropyridine (i.e. thepyrazole product of Step C) (30.4 g, 118 mmol) in dry tetrahydrofuran(250 mL) at −76° C. was added dropwise a solution of lithiumdiisopropylamide (118 mmol) in tetrahydrofuran at such a rate as tomaintain the temperature below −71° C. The reaction mixture was stirredfor 15 minutes at −76° C., and carbon dioxide was then bubbled throughfor 10 minutes, causing warming to −57° C. The reaction mixture waswarmed to −20° C. and quenched with water. The reaction mixture wasconcentrated and then taken up in water (1 L) and ether (500 mL), andthen aqueous 1N sodium hydroxide solution (20 mL) was added. The aqueousextracts were washed with ether and acidified with hydrochloric acid.The precipitated solids were filtered, washed with water and dried toafford the title compound as a tan solid (27.7 g). (Product from anotherrun following a similar procedure melted at 200-201° C.)

¹H NMR (DMSO-d₆) δ 7.25 (s, 1H), 7.68 (dd, 1H), 8.24 (d, 1H), 8.56 (d,1H).

Step E: Preparation of3-Bromo-1-(3-chloro-2-pyridinyl)-N-[2-methyl-6-(3-methyl-1-oxobutyl)phenyl]-1H-pyrazole-5-carboxamide

To a solution of3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxylic acid (i.e. thepyrazole product of Step D) (500 mg, 1.65 mmol) in dichloromethane (10mL) was added 1 drop of N,N-dimethylformamide. Oxalyl Chloride (0.43 mL,5 mmol) was added and the mixture was stirred at 23° C. for 1 hour. Thesolvent was removed under reduced pressure and the residue was dilutedwith acetonitrile (20 mL) and the solvent was again removed underreduced pressure. The residue was dissolved in tetrahydrofuran (10 mL)and treated with 1-(2-amino-3-methylphenyl)-3-methyl-1-butanone,prepared according to Chem. Pharm. Bull., 2000, 48, 1-15, (330 mg, 1.6mmol) and finally triethylamine (0.45 mL, 3.2 mmol). The mixture washeated at 60° C. for 1 hour. The cooled reaction mixture was dilutedwith ethyl acetate (50 mL) and water (50 mL). The organic layer waswashed with water (2×30 mL) and 1N hydrochloric acid (2×30 mL). Theseparated organic layer was dried over magnesium sulfate and evaporatedto dryness under reduced pressure. The residue was subjected to silicagel chromatography using ethyl acetate/hexanes (3:7) as eluent.Appropriate fractions were pooled to afford, after removal of thesolvents, the title compound, a compound of the invention (210 mg), as ayellow solid melting at 119-120° C.

¹H NMR (CDCl₃) δ 0.97 (d, 6H), 2.21 (s, 3H), 2.84 (d, 2H), 7.06 (s, 1H),7.21 (m, 1H), 7.4 (m, 2H), 7.62 (d, 1H), 7.81 (d, 1H), 8.42 (d, 1H),10.6 (br, 1H).

By the procedures described herein together with methods known in theart, the following compounds of Tables 1 to 12 can be prepared. Thefollowing abbreviations are used in the Tables: i means iso, Me meansmethyl, Pr means propyl, i-Pr means isopropyl, Ph means phenyl, OMemeans methoxy, SMe means methylthio, CN means cyano and NO₂ means nitro.

TABLE 1

R^(4a) R^(4b) R³ R^(5a) R^(5b) A is NOMe Me H i-Pr CF₃ 2-Cl-phenyl Cl Hi-Pr CF₃ 2-Cl-phenyl Me Cl i-Pr CF₃ 2-Cl-phenyl Cl Cl i-Pr CF₃2-Cl-phenyl Me Br i-Pr CF₃ 2-Cl-phenyl Cl Br i-Pr CF₃ 2-Cl-phenyl Me Hi-Pr CF₃ 3-Cl-2-pyridyl Cl H i-Pr CF₃ 3-Cl-2-pyridyl Me Cl i-Pr CF₃3-Cl-2-pyridyl Cl Cl i-Pr CF₃ 3-Cl-2-pyridyl Me Br i-Pr CF₃3-Cl-2-pyridyl Cl Br i-Pr CF₃ 3-Cl-2-pyridyl Me H i-Pr Br 2-Cl-phenyl ClH i-Pr Br 2-Cl-phenyl Me Cl i-Pr Br 2-Cl-phenyl Cl Cl i-Pr Br2-Cl-phenyl Me Br i-Pr Br 2-Cl-phenyl Cl Br i-Pr Br 2-Cl-phenyl Me Hi-Pr Br 3-Cl-2-pyridyl Cl H i-Pr Br 3-Cl-2-pyridyl Me Cl i-Pr Br3-Cl-2-pyridyl Cl Cl i-Pr Br 3-Cl-2-pyridyl Me Br i-Pr Br 3-Cl-2-pyridylCl Br i-Pr Br 3-Cl-2-pyridyl Me H i-Pr Cl 2-Cl-phenyl Cl H i-Pr Cl2-Cl-phenyl Me Cl i-Pr Cl 2-Cl-phenyl Cl Cl i-Pr Cl 2-Cl-phenyl Me Bri-Pr Cl 2-Cl-phenyl Cl Br i-Pr Cl 2-Cl-phenyl Me H i-Pr Cl3-Cl-2-pyridyl Cl H i-Pr Cl 3-Cl-2-pyridyl Me Cl i-Pr Cl 3-Cl-2-pyridylCl Cl i-Pr Cl 3-Cl-2-pyridyl Me Br i-Pr Cl 3-Cl-2-pyridyl Cl Br i-Pr Cl3-Cl-2-pyridyl Me H Me CF₃ 2-Cl-phenyl Cl H Me CF₃ 2-Cl-phenyl Me Cl MeCF₃ 2-Cl-phenyl Cl Cl Me CF₃ 2-Cl-phenyl Me Br Me CF₃ 2-Cl-phenyl Cl BrMe CF₃ 2-Cl-phenyl Me H Me CF₃ 3-Cl-2-pyridyl Cl H Me CF₃ 3-Cl-2-pyridylMe Cl Me CF₃ 3-Cl-2-pyridyl Cl Cl Me CF₃ 3-Cl-2-pyridyl Me Br Me CF₃3-Cl-2-pyridyl Cl Br Me CF₃ 3-Cl-2-pyridyl Me H Me Br 2-Cl-phenyl Cl HMe Br 2-Cl-phenyl Me Cl Me Br 2-Cl-phenyl Cl Cl Me Br 2-Cl-phenyl Me BrMe Br 2-Cl-phenyl Cl Br Me Br 2-Cl-phenyl Me H Me Br 3-Cl-2-pyridyl Cl HMe Br 3-Cl-2-pyridyl Me Cl Me Br 3-Cl-2-pyridyl Cl Cl Me Br3-Cl-2-pyridyl Me Br Me Br 3-Cl-2-pyridyl Cl Br Me Br 3-Cl-2-pyridyl MeH Me Cl 2-Cl-phenyl Cl H Me Cl 2-Cl-phenyl Me Cl Me Cl 2-Cl-phenyl Cl ClMe Cl 2-Cl-phenyl Me Br Me Cl 2-Cl-phenyl Cl Br Me Cl 2-Cl-phenyl Me HMe Cl 3-Cl-2-pyridyl Cl H Me Cl 3-Cl-2-pyridyl Me Cl Me Cl3-Cl-2-pyridyl Cl Cl Me Cl 3-Cl-2-pyridyl Me Br Me Cl 3-Cl-2-pyridyl ClBr Me Cl 3-Cl-2-pyridyl Me H i-Pr OCH₂CF₃ 2-Cl-phenyl Cl H i-Pr OCH₂CF₃2-Cl-phenyl Me Cl i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Cl i-Pr OCH₂CF₃2-Cl-phenyl Me Br i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Br i-Pr OCH₂CF₃2-Cl-phenyl Me H i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl H i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Cl i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Br i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Br i-Pr OCH₂CF₃3-Cl-2-pyridyl Me H i-Pr OCHF₂ 2-Cl-phenyl Cl H i-Pr OCHF₂ 2-Cl-phenylMe Cl i-Pr OCHF₂ 2-Cl-phenyl Cl Cl i-Pr OCHF₂ 2-Cl-phenyl Me Br i-PrOCHF₂ 2-Cl-phenyl Cl Br i-Pr OCHF₂ 2-Cl-phenyl Me H i-Pr OCHF₂3-Cl-2-pyridyl Cl H i-Pr OCHF₂ 3-Cl-2-pyridyl Me Cl i-Pr OCHF₂3-Cl-2-pyridyl Cl Cl i-Pr OCHF₂ 3-Cl-2-pyridyl Me Br i-Pr OCHF₂3-Cl-2-pyridyl Cl Br i-Pr OCHF₂ 3-Cl-2-pyridyl Me H Me OCH₂CF₃2-Cl-phenyl Cl H Me OCH₂CF₃ 2-Cl-phenyl Me Cl Me OCH₂CF₃ 2-Cl-phenyl ClCl Me OCH₂CF₃ 2-Cl-phenyl Me Br Me OCH₂CF₃ 2-Cl-phenyl Cl Br Me OCH₂CF₃2-Cl-phenyl Me H Me OCH₂CF₃ 3-Cl-2-pyridyl Cl H Me OCH₂CF₃3-Cl-2-pyridyl Me Cl Me OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl Me OCH₂CF₃3-Cl-2-pyridyl Me Br Me OCH₂CF₃ 3-Cl-2-pyridyl Cl Br Me OCH₂CF₃3-Cl-2-pyridyl Me H Me OCHF₂ 2-Cl-phenyl Cl H Me OCHF₂ 2-Cl-phenyl Me ClMe OCHF₂ 2-Cl-phenyl Cl Cl Me OCHF₂ 2-Cl-phenyl Me Br Me OCHF₂2-Cl-phenyl Cl Br Me OCHF₂ 2-Cl-phenyl Me H Me OCHF₂ 3-Cl-2-pyridyl Cl HMe OCHF₂ 3-Cl-2-pyridyl Me Cl Me OCHF₂ 3-Cl-2-pyridyl Cl Cl Me OCHF₂3-Cl-2-pyridyl Me Br Me OCHF₂ 3-Cl-2-pyridyl Cl Br Me OCHF₂3-Cl-2-pyridyl A is NNMe₂ Me H i-Pr CF₃ 2-Cl-phenyl Cl H i-Pr CF₃2-Cl-phenyl Me Cl i-Pr CF₃ 2-Cl-phenyl Cl Cl i-Pr CF₃ 2-Cl-phenyl Me Bri-Pr CF₃ 2-Cl-phenyl Cl Br i-Pr CF₃ 2-Cl-phenyl Me H i-Pr CF₃3-Cl-2-pyridyl Cl H i-Pr CF₃ 3-Cl-2-pyridyl Me Cl i-Pr CF₃3-Cl-2-pyridyl Cl Cl i-Pr CF₃ 3-Cl-2-pyridyl Me Br i-Pr CF₃3-Cl-2-pyridyl Cl Br i-Pr CF₃ 3-Cl-2-pyridyl Me H i-Pr Br 2-Cl-phenyl ClH i-Pr Br 2-Cl-phenyl Me Cl i-Pr Br 2-Cl-phenyl Cl Cl i-Pr Br2-Cl-phenyl Me Br i-Pr Br 2-Cl-phenyl Cl Br i-Pr Br 2-Cl-phenyl Me Hi-Pr Br 3-Cl-2-pyridyl Cl H i-Pr Br 3-Cl-2-pyridyl Me Cl i-Pr Br3-Cl-2-pyridyl Cl Cl i-Pr Br 3-Cl-2-pyridyl Me Br i-Pr Br 3-Cl-2-pyridylCl Br i-Pr Br 3-Cl-2-pyridyl Me H i-Pr Cl 2-Cl-phenyl Cl H i-Pr Cl2-Cl-phenyl Me Cl i-Pr Cl 2-Cl-phenyl Cl Cl i-Pr Cl 2-Cl-phenyl Me Bri-Pr Cl 2-Cl-phenyl Cl Br i-Pr Cl 2-Cl-phenyl Me H i-Pr Cl3-Cl-2-pyridyl Cl H i-Pr Cl 3-Cl-2-pyridyl Me Cl i-Pr Cl 3-Cl-2-pyridylCl Cl i-Pr Cl 3-Cl-2-pyridyl Me Br i-Pr Cl 3-Cl-2-pyridyl Cl Br i-Pr Cl3-Cl-2-pyridyl Me H Me CF₃ 2-Cl-phenyl Cl H Me CF₃ 2-Cl-phenyl Me Cl MeCF₃ 2-Cl-phenyl Cl Cl Me CF₃ 2-Cl-phenyl Me Br Me CF₃ 2-Cl-phenyl Cl BrMe CF₃ 2-Cl-phenyl Me H Me CF₃ 3-Cl-2-pyridyl Cl H Me CF₃ 3-Cl-2-pyridylMe Cl Me CF₃ 3-Cl-2-pyridyl Cl Cl Me CF₃ 3-Cl-2-pyridyl Me Br Me CF₃3-Cl-2-pyridyl Cl Br Me CF₃ 3-Cl-2-pyridyl Me H Me Br 2-Cl-phenyl Cl HMe Br 2-Cl-phenyl Me Cl Me Br 2-Cl-phenyl Cl Cl Me Br 2-Cl-phenyl Me BrMe Br 2-Cl-phenyl Cl Br Me Br 2-Cl-phenyl Me H Me Br 3-Cl-2-pyridyl Cl HMe Br 3-Cl-2-pyridyl Me Cl Me Br 3-Cl-2-pyridyl Cl Cl Me Br3-Cl-2-pyridyl Me Br Me Br 3-Cl-2-pyridyl Cl Br Me Br 3-Cl-2-pyridyl MeH Me Cl 2-Cl-phenyl Cl H Me Cl 2-Cl-phenyl Me Cl Me Cl 2-Cl-phenyl Cl ClMe Cl 2-Cl-phenyl Me Br Me Cl 2-Cl-phenyl Cl Br Me Cl 2-Cl-phenyl Me HMe Cl 3-Cl-2-pyridyl Cl H Me Cl 3-Cl-2-pyridyl Me Cl Me Cl3-Cl-2-pyridyl Cl Cl Me Cl 3-Cl-2-pyridyl Me Br Me Cl 3-Cl-2-pyridyl ClBr Me Cl 3-Cl-2-pyridyl Me H i-Pr OCH₂CF₃ 2-Cl-phenyl Cl H i-Pr OCH₂CF₃2-Cl-phenyl Me Cl i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Cl i-Pr OCH₂CF₃2-Cl-phenyl Me Br i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Br i-Pr OCH₂CF₃2-Cl-phenyl Me H i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl H i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Cl i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Br i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Br i-Pr OCH₂CF₃3-Cl-2-pyridyl Me H i-Pr OCHF₂ 2-Cl-phenyl Cl H i-Pr OCHF₂ 2-Cl-phenylMe Cl i-Pr OCHF₂ 2-Cl-phenyl Cl Cl i-Pr OCHF₂ 2-Cl-phenyl Me Br i-PrOCHF₂ 2-Cl-phenyl Cl Br i-Pr OCHF₂ 2-Cl-phenyl Me H i-Pr OCHF₂3-Cl-2-pyridyl Cl H i-Pr OCHF₂ 3-Cl-2-pyridyl Me Cl i-Pr OCHF₂3-Cl-2-pyridyl Cl Cl i-Pr OCHF₂ 3-Cl-2-pyridyl Me Br i-Pr OCHF₂3-Cl-2-pyridyl Cl Br i-Pr OCHF₂ 3-Cl-2-pyridyl Me H i-Pr Me 2-Cl-phenylCl H i-Pr Me 2-Cl-phenyl Me Cl i-Pr Me 2-Cl-phenyl Cl Cl Me OCH₂CF₃2-Cl-phenyl Me Br Me OCH₂CF₃ 2-Cl-phenyl Cl Br Me OCH₂CF₃ 2-Cl-phenyl MeH Me OCH₂CF₃ 3-Cl-2-pyridyl Cl H Me OCH₂CF₃ 3-Cl-2-pyridyl Me Cl MeOCH₂CF₃ 3-Cl-2-pyridyl Cl Cl Me OCH₂CF₃ 3-Cl-2-pyridyl Me Br Me OCH₂CF₃3-Cl-2-pyridyl Cl Br Me OCH₂CF₃ 3-Cl-2-pyridyl Me H Me OCHF₂ 2-Cl-phenylCl H Me OCHF₂ 2-Cl-phenyl Me Cl Me OCHF₂ 2-Cl-phenyl Cl Cl Me OCHF₂2-Cl-phenyl Me Br Me OCHF₂ 2-Cl-phenyl Cl Br Me OCHF₂ 2-Cl-phenyl Me HMe OCHF₂ 3-Cl-2-pyridyl Cl H Me OCHF₂ 3-Cl-2-pyridyl Me Cl Me OCHF₂3-Cl-2-pyridyl Cl Cl Me OCHF₂ 3-Cl-2-pyridyl Me Br Me OCHF₂3-Cl-2-pyridyl Cl Br Me OCHF₂ 3-Cl-2-pyridyl A is S═O Me H i-Pr CF₃2-Cl-phenyl Cl H i-Pr CF₃ 2-Cl-phenyl Me Cl i-Pr CF₃ 2-Cl-phenyl Cl Cli-Pr CF₃ 2-Cl-phenyl Me Br i-Pr CF₃ 2-Cl-phenyl Cl Br i-Pr CF₃2-Cl-phenyl Me H i-Pr CF₃ 3-Cl-2-pyridyl Cl H i-Pr CF₃ 3-Cl-2-pyridyl MeCl i-Pr CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr CF₃ 3-Cl-2-pyridyl Me Br i-Pr CF₃3-Cl-2-pyridyl Cl Br i-Pr CF₃ 3-Cl-2-pyridyl Me H i-Pr Br 2-Cl-phenyl ClH i-Pr Br 2-Cl-phenyl Me Cl i-Pr Br 2-Cl-phenyl Cl Cl i-Pr Br2-Cl-phenyl Me Br i-Pr Br 2-Cl-phenyl Cl Br i-Pr Br 2-Cl-phenyl Me Hi-Pr Br 3-Cl-2-pyridyl Cl H i-Pr Br 3-Cl-2-pyridyl Me Cl i-Pr Br3-Cl-2-pyridyl Cl Cl i-Pr Br 3-Cl-2-pyridyl Me Br i-Pr Br 3-Cl-2-pyridylCl Br i-Pr Br 3-Cl-2-pyridyl Me H i-Pr Cl 2-Cl-phenyl Cl H i-Pr Cl2-Cl-phenyl Me Cl i-Pr Cl 2-Cl-phenyl Cl Cl i-Pr Cl 2-Cl-phenyl Me Bri-Pr Cl 2-Cl-phenyl Cl Br i-Pr Cl 2-Cl-phenyl Me H i-Pr Cl3-Cl-2-pyridyl Cl H i-Pr Cl 3-Cl-2-pyridyl Me Cl i-Pr Cl 3-Cl-2-pyridylCl Cl i-Pr Cl 3-Cl-2-pyridyl Me Br i-Pr Cl 3-Cl-2-pyridyl Cl Br i-Pr Cl3-Cl-2-pyridyl Me H Me CF₃ 2-Cl-phenyl Cl H Me CF₃ 2-Cl-phenyl Me Cl MeCF₃ 2-Cl-phenyl Cl Cl Me CF₃ 2-Cl-phenyl Me Br Me CF₃ 2-Cl-phenyl Cl BrMe CF₃ 2-Cl-phenyl Me H Me CF₃ 3-Cl-2-pyridyl Cl H Me CF₃ 3-Cl-2-pyridylMe Cl Me CF₃ 3-Cl-2-pyridyl Cl Cl Me CF₃ 3-Cl-2-pyridyl Me Br Me CF₃3-Cl-2-pyridyl Cl Br Me CF₃ 3-Cl-2-pyridyl Me H Me Br 2-Cl-phenyl Cl HMe Br 2-Cl-phenyl Me Cl Me Br 2-Cl-phenyl Cl Cl Me Br 2-Cl-phenyl Me BrMe Br 2-Cl-phenyl Cl Br Me Br 2-Cl-phenyl Me H Me Br 3-Cl-2-pyridyl Cl HMe Br 3-Cl-2-pyridyl Me Cl Me Br 3-Cl-2-pyridyl Cl Cl Me Br3-Cl-2-pyridyl Me Br Me Br 3-Cl-2-pyridyl Cl Br Me Br 3-Cl-2-pyridyl MeH Me Cl 2-Cl-phenyl Cl H Me Cl 2-Cl-phenyl Me Cl Me Cl 2-Cl-phenyl Cl ClMe Cl 2-Cl-phenyl Me Br Me Cl 2-Cl-phenyl Cl Br Me Cl 2-Cl-phenyl Me HMe Cl 3-Cl-2-pyridyl Cl H Me Cl 3-Cl-2-pyridyl Me Cl Me Cl3-Cl-2-pyridyl Cl Cl Me Cl 3-Cl-2-pyridyl Me Br Me Cl 3-Cl-2-pyridyl ClBr Me Cl 3-Cl-2-pyridyl Me H i-Pr OCH₂CF₃ 2-Cl-phenyl Cl H i-Pr OCH₂CF₃2-Cl-phenyl Me Cl i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Cl i-Pr OCH₂CF₃2-Cl-phenyl Me Br i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Br i-Pr OCH₂CF₃2-Cl-phenyl Me H i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl H i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Cl i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Br i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Br i-Pr OCH₂CF₃3-Cl-2-pyridyl Me H i-Pr OCHF₂ 2-Cl-phenyl Cl H i-Pr OCHF₂ 2-Cl-phenylMe Cl i-Pr OCHF₂ 2-Cl-phenyl Cl Cl i-Pr OCHF₂ 2-Cl-phenyl Me Br i-PrOCHF₂ 2-Cl-phenyl Cl Br i-Pr OCHF₂ 2-Cl-phenyl Me H i-Pr OCHF₂3-Cl-2-pyridyl Cl H i-Pr OCHF₂ 3-Cl-2-pyridyl Me Cl i-Pr OCHF₂3-Cl-2-pyridyl Cl Cl i-Pr OCHF₂ 3-Cl-2-pyridyl Me Br i-Pr OCHF₂3-Cl-2-pyridyl Cl Br i-Pr OCHF₂ 3-Cl-2-pyridyl Me H Me OCH₂CF₃2-Cl-phenyl Cl H Me OCH₂CF₃ 2-Cl-phenyl Me Cl Me OCH₂CF₃ 2-Cl-phenyl ClCl Me OCH₂CF₃ 2-Cl-phenyl Me Br Me OCH₂CF₃ 2-Cl-phenyl Cl Br Me OCH₂CF₃2-Cl-phenyl Me H Me OCH₂CF₃ 3-Cl-2-pyridyl Cl H Me OCH₂CF₃3-Cl-2-pyridyl Me Cl Me OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl Me OCH₂CF₃3-Cl-2-pyridyl Me Br Me OCH₂CF₃ 3-Cl-2-pyridyl Cl Br Me OCH₂CF₃3-Cl-2-pyridyl Me H Me OCHF₂ 2-Cl-phenyl Cl H Me OCHF₂ 2-Cl-phenyl Me ClMe OCHF₂ 2-Cl-phenyl Cl Cl Me OCHF₂ 2-Cl-phenyl Me Br Me OCHF₂2-Cl-phenyl Cl Br Me OCHF₂ 2-Cl-phenyl Me H Me OCHF₂ 3-Cl-2-pyridyl Cl HMe OCHF₂ 3-Cl-2-pyridyl Me Cl Me OCHF₂ 3-Cl-2-pyridyl Cl Cl Me OCHF₂3-Cl-2-pyridyl Me Br Me OCHF₂ 3-Cl-2-pyridyl Cl Br Me OCHF₂3-Cl-2-pyridyl A is N—CN Me H i-Pr CF₃ 2-Cl-phenyl Cl H i-Pr CF₃2-Cl-phenyl Me Cl i-Pr CF₃ 2-Cl-phenyl Cl Cl i-Pr CF₃ 2-Cl-phenyl Me Bri-Pr CF₃ 2-Cl-phenyl Cl Br i-Pr CF₃ 2-Cl-phenyl Me H i-Pr CF₃3-Cl-2-pyridyl Cl H i-Pr CF₃ 3-Cl-2-pyridyl Me Cl i-Pr CF₃3-Cl-2-pyridyl Cl Cl i-Pr CF₃ 3-Cl-2-pyridyl Me Br i-Pr CF₃3-Cl-2-pyridyl Cl Br i-Pr CF₃ 3-Cl-2-pyridyl Me H i-Pr Br 2-Cl-phenyl ClH i-Pr Br 2-Cl-phenyl Me Cl i-Pr Br 2-Cl-phenyl Cl Cl i-Pr Br2-Cl-phenyl Me Br i-Pr Br 2-Cl-phenyl Cl Br i-Pr Br 2-Cl-phenyl Me Hi-Pr Br 3-Cl-2-pyridyl Cl H i-Pr Br 3-Cl-2-pyridyl Me Cl i-Pr Br3-Cl-2-pyridyl Cl Cl i-Pr Br 3-Cl-2-pyridyl Me Br i-Pr Br 3-Cl-2-pyridylCl Br i-Pr Br 3-Cl-2-pyridyl Me H i-Pr Cl 2-Cl-phenyl Cl H i-Pr Cl2-Cl-phenyl Me Cl i-Pr Cl 2-Cl-phenyl Cl Cl i-Pr Cl 2-Cl-phenyl Me Bri-Pr Cl 2-Cl-phenyl Cl Br i-Pr Cl 2-Cl-phenyl Me H i-Pr Cl3-Cl-2-pyridyl Cl H i-Pr Cl 3-Cl-2-pyridyl Me Cl i-Pr Cl 3-Cl-2-pyridylCl Cl i-Pr Cl 3-Cl-2-pyridyl Me Br i-Pr Cl 3-Cl-2-pyridyl Cl Br i-Pr Cl3-Cl-2-pyridyl Me H Me CF₃ 2-Cl-phenyl Cl H Me CF₃ 2-Cl-phenyl Me Cl MeCF₃ 2-Cl-phenyl Cl Cl Me CF₃ 2-Cl-phenyl Me Br Me CF₃ 2-Cl-phenyl Cl BrMe CF₃ 2-Cl-phenyl Me H Me CF₃ 3-Cl-2-pyridyl Cl H Me CF₃ 3-Cl-2-pyridylMe Cl Me CF₃ 3-Cl-2-pyridyl Cl Cl Me CF₃ 3-Cl-2-pyridyl Me Br Me CF₃3-Cl-2-pyridyl Cl Br Me CF₃ 3-Cl-2-pyridyl Me H Me Br 2-Cl-phenyl Cl HMe Br 2-Cl-phenyl Me Cl Me Br 2-Cl-phenyl Cl Cl Me Br 2-Cl-phenyl Me BrMe Br 2-Cl-phenyl Cl Br Me Br 2-Cl-phenyl Me H Me Br 3-Cl-2-pyridyl Cl HMe Br 3-Cl-2-pyridyl Me Cl Me Br 3-Cl-2-pyridyl Cl Cl Me Br3-Cl-2-pyridyl Me Br Me Br 3-Cl-2-pyridyl Cl Br Me Br 3-Cl-2-pyridyl MeH Me Cl 2-Cl-phenyl Cl H Me Cl 2-Cl-phenyl Me Cl Me Cl 2-Cl-phenyl Cl ClMe Cl 2-Cl-phenyl Me Br Me Cl 2-Cl-phenyl Cl Br Me Cl 2-Cl-phenyl Me HMe Cl 3-Cl-2-pyridyl Cl H Me Cl 3-Cl-2-pyridyl Me Cl Me Cl3-Cl-2-pyridyl Cl Cl Me Cl 3-Cl-2-pyridyl Me Br Me Cl 3-Cl-2-pyridyl ClBr Me Cl 3-Cl-2-pyridyl Me H i-Pr OCH₂CF₃ 2-Cl-phenyl Cl H i-Pr OCH₂CF₃2-Cl-phenyl Me Cl i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Cl i-Pr OCH₂CF₃2-Cl-phenyl Me Br i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Br i-Pr OCH₂CF₃2-Cl-phenyl Me H i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl H i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Cl i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Br i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Br i-Pr OCH₂CF₃3-Cl-2-pyridyl Me H i-Pr OCHF₂ 2-Cl-phenyl Cl H i-Pr OCHF₂ 2-Cl-phenylMe Cl i-Pr OCHF₂ 2-Cl-phenyl Cl Cl i-Pr OCHF₂ 2-Cl-phenyl Me Br i-PrOCHF₂ 2-Cl-phenyl Cl Br i-Pr OCHF₂ 2-Cl-phenyl Me H i-Pr OCHF₂3-Cl-2-pyridyl Cl H i-Pr OCHF₂ 3-Cl-2-pyridyl Me Cl i-Pr OCHF₂3-Cl-2-pyridyl Cl Cl i-Pr OCHF₂ 3-Cl-2-pyridyl Me Br i-Pr OCHF₂3-Cl-2-pyridyl Cl Br i-Pr OCHF₂ 3-Cl-2-pyridyl Me H i-Pr Me 2-Cl-phenylCl H i-Pr Me 2-Cl-phenyl Me Cl i-Pr Me 2-Cl-phenyl Cl Cl Me OCH₂CF₃2-Cl-phenyl Me Br Me OCH₂CF₃ 2-Cl-phenyl Cl Br Me OCH₂CF₃ 2-Cl-phenyl MeH Me OCH₂CF₃ 3-Cl-2-pyridyl Cl H Me OCH₂CF₃ 3-Cl-2-pyridyl Me Cl MeOCH₂CF₃ 3-Cl-2-pyridyl Cl Cl Me OCH₂CF₃ 3-Cl-2-pyridyl Me Br Me OCH₂CF₃3-Cl-2-pyridyl Cl Br Me OCH₂CF₃ 3-Cl-2-pyridyl Me H Me OCHF₂ 2-Cl-phenylCl H Me OCHF₂ 2-Cl-phenyl Me Cl Me OCHF₂ 2-Cl-phenyl Cl Cl Me OCHF₂2-Cl-phenyl Me Br Me OCHF₂ 2-Cl-phenyl Cl Br Me OCHF₂ 2-Cl-phenyl Me HMe OCHF₂ 3-Cl-2-pyridyl Cl H Me OCHF₂ 3-Cl-2-pyridyl Me Cl Me OCHF₂3-Cl-2-pyridyl Cl Cl Me OCHF₂ 3-Cl-2-pyridyl Me Br Me OCHF₂3-Cl-2-pyridyl Cl Br Me OCHF₂ 3-Cl-2-pyridyl A is N—NO₂ Me H i-Pr CF₃2-Cl-phenyl Cl H i-Pr CF₃ 2-Cl-phenyl Me Cl i-Pr CF₃ 2-Cl-phenyl Cl Cli-Pr CF₃ 2-Cl-phenyl Me Br i-Pr CF₃ 2-Cl-phenyl Cl Br i-Pr CF₃2-Cl-phenyl Me H i-Pr CF₃ 3-Cl-2-pyridyl Cl H i-Pr CF₃ 3-Cl-2-pyridyl MeCl i-Pr CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr CF₃ 3-Cl-2-pyridyl Me Br i-Pr CF₃3-Cl-2-pyridyl Cl Br i-Pr CF₃ 3-Cl-2-pyridyl Me H i-Pr Br 2-Cl-phenyl ClH i-Pr Br 2-Cl-phenyl Me Cl i-Pr Br 2-Cl-phenyl Cl Cl i-Pr Br2-Cl-phenyl Me Br i-Pr Br 2-Cl-phenyl Cl Br i-Pr Br 2-Cl-phenyl Me Hi-Pr Br 3-Cl-2-pyridyl Cl H i-Pr Br 3-Cl-2-pyridyl Me Cl i-Pr Br3-Cl-2-pyridyl Cl Cl i-Pr Br 3-Cl-2-pyridyl Me Br i-Pr Br 3-Cl-2-pyridylCl Br i-Pr Br 3-Cl-2-pyridyl Me H i-Pr Cl 2-Cl-phenyl Cl H i-Pr Cl2-Cl-phenyl Me Cl i-Pr Cl 2-Cl-phenyl Cl Cl i-Pr Cl 2-Cl-phenyl Me Bri-Pr Cl 2-Cl-phenyl Cl Br i-Pr Cl 2-Cl-phenyl Me H i-Pr Cl3-Cl-2-pyridyl Cl H i-Pr Cl 3-Cl-2-pyridyl Me Cl i-Pr Cl 3-Cl-2-pyridylCl Cl i-Pr Cl 3-Cl-2-pyridyl Me Br i-Pr Cl 3-Cl-2-pyridyl Cl Br i-Pr Cl3-Cl-2-pyridyl Me H Me CF₃ 2-Cl-phenyl Cl H Me CF₃ 2-Cl-phenyl Me Cl MeCF₃ 2-Cl-phenyl Cl Cl Me CF₃ 2-Cl-phenyl Me Br Me CF₃ 2-Cl-phenyl Cl BrMe CF₃ 2-Cl-phenyl Me H Me CF₃ 3-Cl-2-pyridyl Cl H Me CF₃ 3-Cl-2-pyridylMe Cl Me CF₃ 3-Cl-2-pyridyl Cl Cl Me CF₃ 3-Cl-2-pyridyl Me Br Me CF₃3-Cl-2-pyridyl Cl Br Me CF₃ 3-Cl-2-pyridyl Me H Me Br 2-Cl-phenyl Cl HMe Br 2-Cl-phenyl Me Cl Me Br 2-Cl-phenyl Cl Cl Me Br 2-Cl-phenyl Me BrMe Br 2-Cl-phenyl Cl Br Me Br 2-Cl-phenyl Me H Me Br 3-Cl-2-pyridyl Cl HMe Br 3-Cl-2-pyridyl Me Cl Me Br 3-Cl-2-pyridyl Cl Cl Me Br3-Cl-2-pyridyl Me Br Me Br 3-Cl-2-pyridyl Cl Br Me Br 3-Cl-2-pyridyl MeH Me Cl 2-Cl-phenyl Cl H Me Cl 2-Cl-phenyl Me Cl Me Cl 2-Cl-phenyl Cl ClMe Cl 2-Cl-phenyl Me Br Me Cl 2-Cl-phenyl Cl Br Me Cl 2-Cl-phenyl Me HMe Cl 3-Cl-2-pyridyl Cl H Me Cl 3-Cl-2-pyridyl Me Cl Me Cl3-Cl-2-pyridyl Cl Cl Me Cl 3-Cl-2-pyridyl Me Br Me Cl 3-Cl-2-pyridyl ClBr Me Cl 3-Cl-2-pyridyl Me H i-Pr OCH₂CF₃ 2-Cl-phenyl Cl H i-Pr OCH₂CF₃2-Cl-phenyl Me Cl i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Cl i-Pr OCH₂CF₃2-Cl-phenyl Me Br i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Br i-Pr OCH₂CF₃2-Cl-phenyl Me H i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl H i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Cl i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Br i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Br i-Pr OCH₂CF₃3-Cl-2-pyridyl Me H i-Pr OCHF₂ 2-Cl-phenyl Cl H i-Pr OCHF₂ 2-Cl-phenylMe Cl i-Pr OCHF₂ 2-Cl-phenyl Cl Cl i-Pr OCHF₂ 2-Cl-phenyl Me Br i-PrOCHF₂ 2-Cl-phenyl Cl Br i-Pr OCHF₂ 2-Cl-phenyl Me H i-Pr OCHF₂3-Cl-2-pyridyl Cl H i-Pr OCHF₂ 3-Cl-2-pyridyl Me Cl i-Pr OCHF₂3-Cl-2-pyridyl Cl Cl i-Pr OCHF₂ 3-Cl-2-pyridyl Me Br i-Pr OCHF₂3-Cl-2-pyridyl Cl Br i-Pr OCHF₂ 3-Cl-2-pyridyl Me H Me OCH₂CF₃2-Cl-phenyl Cl H Me OCH₂CF₃ 2-Cl-phenyl Me Cl Me OCH₂CF₃ 2-Cl-phenyl ClCl Me OCH₂CF₃ 2-Cl-phenyl Me Br Me OCH₂CF₃ 2-Cl-phenyl Cl Br Me OCH₂CF₃2-Cl-phenyl Me H Me OCH₂CF₃ 3-Cl-2-pyridyl Cl H Me OCH₂CF₃3-Cl-2-pyridyl Me Cl Me OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl Me OCH₂CF₃3-Cl-2-pyridyl Me Br Me OCH₂CF₃ 3-Cl-2-pyridyl Cl Br Me OCH₂CF₃3-Cl-2-pyridyl Me H Me OCHF₂ 2-Cl-phenyl Cl H Me OCHF₂ 2-Cl-phenyl Me ClMe OCHF₂ 2-Cl-phenyl Cl Cl Me OCHF₂ 2-Cl-phenyl Me Br Me OCHF₂2-Cl-phenyl Cl Br Me OCHF₂ 2-Cl-phenyl Me H Me OCHF₂ 3-Cl-2-pyridyl Cl HMe OCHF₂ 3-Cl-2-pyridyl Me Cl Me OCHF₂ 3-Cl-2-pyridyl Cl Cl Me OCHF₂3-Cl-2-pyridyl Me Br Me OCHF₂ 3-Cl-2-pyridyl Cl Br Me OCHF₂3-Cl-2-pyridyl A is NMe Me H i-Pr CF₃ 2-Cl-phenyl Cl H i-Pr CF₃2-Cl-phenyl Me Cl i-Pr CF₃ 2-Cl-phenyl Cl Cl i-Pr CF₃ 2-Cl-phenyl Me Bri-Pr CF₃ 2-Cl-phenyl Cl Br i-Pr CF₃ 2-Cl-phenyl Me H i-Pr CF₃3-Cl-2-pyridyl Cl H i-Pr CF₃ 3-Cl-2-pyridyl Me Cl i-Pr CF₃3-Cl-2-pyridyl Cl Cl i-Pr CF₃ 3-Cl-2-pyridyl Me Br i-Pr CF₃3-Cl-2-pyridyl Cl Br i-Pr CF₃ 3-Cl-2-pyridyl Me H i-Pr Br 2-Cl-phenyl ClH i-Pr Br 2-Cl-phenyl Me Cl i-Pr Br 2-Cl-phenyl Cl Cl i-Pr Br2-Cl-phenyl Me Br i-Pr Br 2-Cl-phenyl Cl Br i-Pr Br 2-Cl-phenyl Me Hi-Pr Br 3-Cl-2-pyridyl Cl H i-Pr Br 3-Cl-2-pyridyl Me Cl i-Pr Br3-Cl-2-pyridyl Cl Cl i-Pr Br 3-Cl-2-pyridyl Me Br i-Pr Br 3-Cl-2-pyridylCl Br i-Pr Br 3-Cl-2-pyridyl Me H i-Pr Cl 2-Cl-phenyl Cl H i-Pr Cl2-Cl-phenyl Me Cl i-Pr Cl 2-Cl-phenyl Cl Cl i-Pr Cl 2-Cl-phenyl Me Bri-Pr Cl 2-Cl-phenyl Cl Br i-Pr Cl 2-Cl-phenyl Me H i-Pr Cl3-Cl-2-pyridyl Cl H i-Pr Cl 3-Cl-2-pyridyl Me Cl i-Pr Cl 3-Cl-2-pyridylCl Cl i-Pr Cl 3-Cl-2-pyridyl Me Br i-Pr Cl 3-Cl-2-pyridyl Cl Br i-Pr Cl3-Cl-2-pyridyl Me H Me CF₃ 2-Cl-phenyl Cl H Me CF₃ 2-Cl-phenyl Me Cl MeCF₃ 2-Cl-phenyl Cl Cl Me CF₃ 2-Cl-phenyl Me Br Me CF₃ 2-Cl-phenyl Cl BrMe CF₃ 2-Cl-phenyl Me H Me CF₃ 3-Cl-2-pyridyl Cl H Me CF₃ 3-Cl-2-pyridylMe Cl Me CF₃ 3-Cl-2-pyridyl Cl Cl Me CF₃ 3-Cl-2-pyridyl Me Br Me CF₃3-Cl-2-pyridyl Cl Br Me CF₃ 3-Cl-2-pyridyl Me H Me Br 2-Cl-phenyl Cl HMe Br 2-Cl-phenyl Me Cl Me Br 2-Cl-phenyl Cl Cl Me Br 2-Cl-phenyl Me BrMe Br 2-Cl-phenyl Cl Br Me Br 2-Cl-phenyl Me H Me Br 3-Cl-2-pyridyl Cl HMe Br 3-Cl-2-pyridyl Me Cl Me Br 3-Cl-2-pyridyl Cl Cl Me Br3-Cl-2-pyridyl Me Br Me Br 3-Cl-2-pyridyl Cl Br Me Br 3-Cl-2-pyridyl MeH Me Cl 2-Cl-phenyl Cl H Me Cl 2-Cl-phenyl Me Cl Me Cl 2-Cl-phenyl Cl ClMe Cl 2-Cl-phenyl Me Br Me Cl 2-Cl-phenyl Cl Br Me Cl 2-Cl-phenyl Me HMe Cl 3-Cl-2-pyridyl Cl H Me Cl 3-Cl-2-pyridyl Me Cl Me Cl3-Cl-2-pyridyl Cl Cl Me Cl 3-Cl-2-pyridyl Me Br Me Cl 3-Cl-2-pyridyl ClBr Me Cl 3-Cl-2-pyridyl Me H i-Pr OCH₂CF₃ 2-Cl-phenyl Cl H i-Pr OCH₂CF₃2-Cl-phenyl Me Cl i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Cl i-Pr OCH₂CF₃2-Cl-phenyl Me Br i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Br i-Pr OCH₂CF₃2-Cl-phenyl Me H i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl H i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Cl i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Br i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Br i-Pr OCH₂CF₃3-Cl-2-pyridyl Me H i-Pr OCHF₂ 2-Cl-phenyl Cl H i-Pr OCHF₂ 2-Cl-phenylMe Cl i-Pr OCHF₂ 2-Cl-phenyl Cl Cl i-Pr OCHF₂ 2-Cl-phenyl Me Br i-PrOCHF₂ 2-Cl-phenyl Cl Br i-Pr OCHF₂ 2-Cl-phenyl Me H i-Pr OCHF₂3-Cl-2-pyridyl Cl H i-Pr OCHF₂ 3-Cl-2-pyridyl Me Cl i-Pr OCHF₂3-Cl-2-pyridyl Cl Cl i-Pr OCHF₂ 3-Cl-2-pyridyl Me Br i-Pr OCHF₂3-Cl-2-pyridyl Cl Br i-Pr OCHF₂ 3-Cl-2-pyridyl Me H i-Pr Me 2-Cl-phenylCl H i-Pr Me 2-Cl-phenyl Me Cl i-Pr Me 2-Cl-phenyl Cl Cl Me OCH₂CF₃2-Cl-phenyl Me Br Me OCH₂CF₃ 2-Cl-phenyl Cl Br Me OCH₂CF₃ 2-Cl-phenyl MeH Me OCH₂CF₃ 3-Cl-2-pyridyl Cl H Me OCH₂CF₃ 3-Cl-2-pyridyl Me Cl MeOCH₂CF₃ 3-Cl-2-pyridyl Cl Cl Me OCH₂CF₃ 3-Cl-2-pyridyl Me Br Me OCH₂CF₃3-Cl-2-pyridyl Cl Br Me OCH₂CF₃ 3-Cl-2-pyridyl Me H Me OCHF₂ 2-Cl-phenylCl H Me OCHF₂ 2-Cl-phenyl Me Cl Me OCHF₂ 2-Cl-phenyl Cl Cl Me OCHF₂2-Cl-phenyl Me Br Me OCHF₂ 2-Cl-phenyl Cl Br Me OCHF₂ 2-Cl-phenyl Me HMe OCHF₂ 3-Cl-2-pyridyl Cl H Me OCHF₂ 3-Cl-2-pyridyl Me Cl Me OCHF₂3-Cl-2-pyridyl Cl Cl Me OCHF₂ 3-Cl-2-pyridyl Me Br Me OCHF₂3-Cl-2-pyridyl Cl Br Me OCHF₂ 3-Cl-2-pyridyl

TABLE 2

R^(4a) R^(4b) R³ R^(5a) R^(5b) GR⁶ is OMe Me H i-Pr CF₃ 2-Cl-phenyl Cl Hi-Pr CF₃ 2-Cl-phenyl Me Cl i-Pr CF₃ 2-Cl-phenyl Cl Cl i-Pr CF₃2-Cl-phenyl Me Br i-Pr CF₃ 2-Cl-phenyl Cl Br i-Pr CF₃ 2-Cl-phenyl Me Hi-Pr CF₃ 3-Cl-2-pyridyl Cl H i-Pr CF₃ 3-Cl-2-pyridyl Me Cl i-Fr CF₃3-Cl-2-pyridyl Cl Cl i-Pr CF₃ 3-Cl-2-pyridyl Me Br i-Pr CF₃3-Cl-2-pyridyl Cl Br i-Pr CF₃ 3-Cl-2-pyridyl Me H i-Pr Br 2-Cl-phenyl ClH i-Pr Br 2-Cl-phenyl Me Cl i-Pr Br 2-Cl-phenyl Cl Cl i-Pr Br2-Cl-phenyl Me Br i-Pr Br 2-Cl-phenyl Cl Br i-Pr Br 2-Cl-phenyl Me Hi-Pr Br 3-Cl-2-pyridyl Cl H i-Pr Br 3-Cl-2-pyridyl Me Cl i-Pr Br3-Cl-2-pyridyl Cl Cl i-Pr Br 3-Cl-2-pyridyl Me Br i-Pr Br 3-Cl-2-pyridylCl Br i-Pr Br 3-Cl-2-pyridyl Me H i-Pr Cl 2-Cl-phenyl Cl H i-Pr Cl2-Cl-phenyl Me Cl i-Pr Cl 2-Cl-phenyl Cl Cl i-Pr Cl 2-Cl-phenyl Me Bri-Pr Cl 2-Cl-phenyl Cl Br i-Pr Cl 2-Cl-phenyl Me H i-Pr Cl3-Cl-2-pyridyl Cl H i-Pr Cl 3-Cl-2-pyridyl Me Cl i-Pr Cl 3-Cl-2-pyridylCl Cl i-Pr Cl 3-Cl-2-pyridyl Me Br i-Pr Cl 3-Cl-2-pyridyl Cl Br i-Pr Cl3-Cl-2-pyridyl Me H Me CF₃ 2-Cl-phenyl Cl H Me CF₃ 2-Cl-phenyl Me Cl MeCF₃ 2-Cl-phenyl Cl Cl Me CF₃ 2-Cl-phenyl Me Br Me CF₃ 2-Cl-phenyl Cl BrMe CF₃ 2-Cl-phenyl Me H Me CF₃ 3-Cl-2-pyridyl Cl H Me CF₃ 3-Cl-2-pyridylMe Cl Me CF₃ 3-Cl-2-pyridyl Cl Cl Me CF₃ 3-Cl-2-pyridyl Me Br Me CF₃3-Cl-2-pyridyl Cl Br Me CF₃ 3-Cl-2-pyridyl Me H Me Br 2-Cl-phenyl Cl HMe Br 2-Cl-phenyl Me Cl Me Br 2-Cl-phenyl Cl Cl Me Br 2-Cl-phenyl Me BrMe Br 2-Cl-phenyl Cl Br Me Br 2-Cl-phenyl Me H Me Br 3-Cl-2-pyridyl Cl HMe Br 3-Cl-2-pyridyl Me Cl Me Br 3-Cl-2-pyridyl Cl Cl Me Br3-Cl-2-pyridyl Me Br Me Br 3-Cl-2-pyridyl Cl Br Me Br 3-Cl-2-pyridyl MeH Me Cl 2-Cl-phenyl Cl H Me Cl 2-Cl-phenyl Me Cl Me Cl 2-Cl-phenyl Cl ClMe Cl 2-Cl-phenyl Me Br Me Cl 2-Cl-phenyl Cl Br Me Cl 2-Cl-phenyl Me HMe Cl 3-Cl-2-pyridyl Cl H Me Cl 3-Cl-2-pyridyl Me Cl Me Cl3-Cl-2-pyridyl Cl Cl Me Cl 3-Cl-2-pyridyl Me Br Me Cl 3-Cl-2-pyridyl ClBr Me Cl 3-Cl-2-pyridyl Me H i-Pr OCH₂CF₃ 2-Cl-phenyl Cl H i-Pr OCH₂CF₃2-Cl-phenyl Me Cl i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Cl i-Pr OCH₂CF₃2-Cl-phenyl Me Br i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Br i-Pr OCH₂CF₃2-Cl-phenyl Me H i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl H i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Cl i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Br i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Br i-Pr OCH₂CF₃3-Cl-2-pyridyl Me H i-Pr OCHF₂ 2-Cl-phenyl Cl H i-Pr OCHF₂ 2-Cl-phenylMe Cl i-Pr OCHF₂ 2-Cl-phenyl Cl Cl i-Pr OCHF₂ 2-Cl-phenyl Me Br i-PrOCHF₂ 2-Cl-phenyl Cl Br i-Pr OCHF₂ 2-Cl-phenyl Me H i-Pr OCHF₂3-Cl-2-pyridyl Cl H i-Pr OCHF₂ 3-Cl-2-pyridyl Me Cl i-Pr OCHF₂3-Cl-2-pyridyl Cl Cl i-Pr OCHF₂ 3-Cl-2-pyridyl Me Br i-Pr OCHF₂3-Cl-2-pyridyl Cl Br i-Pr OCHF₂ 3-Cl-2-pyridyl Me H Me OCH₂CF₃2-Cl-phenyl Cl H Me OCH₂CF₃ 2-Cl-phenyl Me Cl Me OCH₂CF₃ 2-Cl-phenyl ClCl Me OCH₂CF₃ 2-Cl-phenyl Me Br Me OCH₂CF₃ 2-Cl-phenyl Cl Br Me OCH₂CF₃2-Cl-phenyl Me H Me OCH₂CF₃ 3-Cl-2-pyridyl Cl H Me OCH₂CF₃3-Cl-2-pyridyl Me Cl Me OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl Me OCH₂CF₃3-Cl-2-pyridyl Me Br Me OCH₂CF₃ 3-Cl-2-pyridyl Cl Br Me OCH₂CF₃3-Cl-2-pyridyl Me H Me OCHF₂ 2-Cl-phenyl Cl H Me OCHF₂ 2-Cl-phenyl Me ClMe OCHF₂ 2-Cl-phenyl Cl Cl Me OCHF₂ 2-Cl-phenyl Me Br Me OCHF₂2-Cl-phenyl Cl Br Me OCHF₂ 2-Cl-phenyl Me H Me OCHF₂ 3-Cl-2-pyridyl Cl HMe OCHF₂ 3-Cl-2-pyridyl Me Cl Me OCHF₂ 3-Cl-2-pyridyl Cl Cl Me OCHF₂3-Cl-2-pyridyl Me Br Me OCHF₂ 3-Cl-2-pyridyl GR⁶ is SMe Me H i-Pr CF₃2-Cl-phenyl Cl H i-Pr CF₃ 2-Cl-phenyl Me Cl i-Pr CF₃ 2-Cl-phenyl Cl Cli-Pr CF₃ 2-Cl-phenyl Me Br i-Pr CF₃ 2-Cl-phenyl Cl Br i-Pr CF₃2-Cl-phenyl Me H i-Pr CF₃ 3-Cl-2-pyridyl Cl H i-Pr CF₃ 3-Cl-2-pyridyl MeCl i-Pr CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr CF₃ 3-Cl-2-pyridyl Me Br i-Pr CF₃3-Cl-2-pyridyl Cl Br i-Pr CF₃ 3-Cl-2-pyridyl Me H i-Pr Br 2-Cl-phenyl ClH i-Pr Br 2-Cl-phenyl Me Cl i-Pr Br 2-Cl-phenyl Cl Cl i-Pr Br2-Cl-phenyl Me Br i-Pr Br 2-Cl-phenyl Cl Br i-Pr Br 2-Cl-phenyl Me Hi-Pr Br 3-Cl-2-pyridyl Cl H i-Pr Br 3-Cl-2-pyridyl Me Cl i-Pr Br3-Cl-2-pyridyl Cl Cl i-Pr Br 3-Cl-2-pyridyl Me Br i-Pr Br 3-Cl-2-pyridylCl Br i-Pr Br 3-Cl-2-pyridyl Me H i-Pr Cl 2-Cl-phenyl Cl H i-Pr Cl2-Cl-phenyl Me Cl i-Pr Cl 2-Cl-phenyl Cl Cl i-Pr Cl 2-Cl-phenyl Me Bri-Pr Cl 2-Cl-phenyl Cl Br i-Pr Cl 2-Cl-phenyl Me H i-Pr Cl3-Cl-2-pyridyl Cl H i-Pr Cl 3-Cl-2-pyridyl Me Cl i-Pr Cl 3-Cl-2-pyridylCl Cl i-Pr Cl 3-Cl-2-pyridyl Me Br i-Pr Cl 3-Cl-2-pyridyl Cl Br i-Pr Cl3-Cl-2-pyridyl Me H Me CF₃ 2-Cl-phenyl Cl H Me CF₃ 2-Cl-phenyl Me Cl MeCF₃ 2-Cl-phenyl Cl Cl Me CF₃ 2-Cl-phenyl Me Br Me CF₃ 2-Cl-phenyl Cl BrMe CF₃ 2-Cl-phenyl Me H Me CF₃ 3-Cl-2-pyridyl Cl H Me CF₃ 3-Cl-2-pyridylMe Cl Me CF₃ 3-Cl-2-pyridyl Cl Cl Me CF₃ 3-Cl-2-pyridyl Me Br Me CF₃3-Cl-2-pyridyl Cl Br Me CF₃ 3-Cl-2-pyridyl Me H Me Br 2-Cl-phenyl Cl HMe Br 2-Cl-phenyl Me Cl Me Br 2-Cl-phenyl Cl Cl Me Br 2-Cl-phenyl Me BrMe Br 2-Cl-phenyl Cl Br Me Br 2-Cl-phenyl Me H Me Br 3-Cl-2-pyridyl Cl HMe Br 3-Cl-2-pyridyl Me Cl Me Br 3-Cl-2-pyridyl Cl Cl Me Br3-Cl-2-pyridyl Me Br Me Br 3-Cl-2-pyridyl Cl Br Me Br 3-Cl-2-pyridyl MeH Me Cl 2-Cl-phenyl Cl H Me Cl 2-Cl-phenyl Me Cl Me Cl 2-Cl-phenyl Cl ClMe Cl 2-Cl-phenyl Me Br Me Cl 2-Cl-phenyl Cl Br Me Cl 2-Cl-phenyl Me HMe Cl 3-Cl-2-pyridyl Cl H Me Cl 3-Cl-2-pyridyl Me Cl Me Cl3-Cl-2-pyridyl Cl Cl Me Cl 3-Cl-2-pyridyl Me Br Me Cl 3-Cl-2-pyridyl ClBr Me Cl 3-Cl-2-pyridyl Me H i-Pr OCH₂CF₃ 2-Cl-phenyl Cl H i-Pr OCH₂CF₃2-Cl-phenyl Me Cl i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Cl i-Pr OCH₂CF₃2-Cl-phenyl Me Br i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Br i-Pr OCH₂CF₃2-Cl-phenyl Me H i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl H i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Cl i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Br i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Br i-Pr OCH₂CF₃3-Cl-2-pyridyl Me H i-Pr OCHF₂ 2-Cl-phenyl Cl H i-Pr OCHF₂ 2-Cl-phenylMe Cl i-Pr OCHF₂ 2-Cl-phenyl Cl Cl i-Pr OCHF₂ 2-Cl-phenyl Me Br i-PrOCHF₂ 2-Cl-phenyl Cl Br i-Pr OCHF₂ 2-Cl-phenyl Me H i-Pr OCHF₂3-Cl-2-pyridyl Cl H i-Pr OCHF₂ 3-Cl-2-pyridyl Me Cl i-Pr OCHF₂3-Cl-2-pyridyl Cl Cl i-Pr OCHF₂ 3-Cl-2-pyridyl Me Br i-Pr OCHF₂3-Cl-2-pyridyl Cl Br i-Pr OCHF₂ 3-Cl-2-pyridyl Me H i-Pr Me 2-Cl-phenylCl H i-Pr Me 2-Cl-phenyl Me Cl i-Pr Me 2-Cl-phenyl Cl Cl Me OCH₂CF₃2-Cl-phenyl Me Br Me OCH₂CF₃ 2-Cl-phenyl Cl Br Me OCH₂CF₃ 2-Cl-phenyl MeH Me OCH₂CF₃ 3-Cl-2-pyridyl Cl H Me OCH₂CF₃ 3-Cl-2-pyridyl Me Cl MeOCH₂CF₃ 3-Cl-2-pyridyl Cl Cl Me OCH₂CF₃ 3-Cl-2-pyridyl Me Br Me OCH₂CF₃3-Cl-2-pyridyl Cl Br Me OCH₂CF₃ 3-Cl-2-pyridyl Me H Me OCHF₂ 2-Cl-phenylCl H Me OCHF₂ 2-Cl-phenyl Me Cl Me OCHF₂ 2-Cl-phenyl Cl Cl Me OCHF₂2-Cl-phenyl Me Br Me OCHF₂ 2-Cl-phenyl Cl Br Me OCHF₂ 2-Cl-phenyl Me HMe OCHF₂ 3-Cl-2-pyridyl Cl H Me OCHF₂ 3-Cl-2-pyridyl Me Cl Me OCHF₂3-Cl-2-pyridyl Cl Cl Me OCHF₂ 3-Cl-2-pyridyl Me Br Me OCHF₂3-Cl-2-pyridyl Cl Br Me OCHF₂ 3-Cl-2-pyridyl GR⁶ is SCH₂Ph Me H i-Pr CF₃2-Cl-phenyl Cl H i-Pr CF₃ 2-Cl-phenyl Me Cl i-Pr CF₃ 2-Cl-phenyl Cl Cli-Pr CF₃ 2-Cl-phenyl Me Br i-Pr CF₃ 2-Cl-phenyl Cl Br i-Pr CF₃2-Cl-phenyl Me H i-Pr CF₃ 3-Cl-2-pyridyl Cl H i-Pr CF₃ 3-Cl-2-pyridyl MeCl i-Pr CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr CF₃ 3-Cl-2-pyridyl Me Br i-Pr CF₃3-Cl-2-pyridyl Cl Br i-Pr CF₃ 3-Cl-2-pyridyl Me H i-Pr Br 2-Cl-phenyl ClH i-Pr Br 2-Cl-phenyl Me Cl i-Pr Br 2-Cl-phenyl Cl Cl i-Pr Br2-Cl-phenyl Me Br i-Pr Br 2-Cl-phenyl Cl Br i-Pr Br 2-Cl-phenyl Me Hi-Pr Br 3-Cl-2-pyridyl Cl H i-Pr Br 3-Cl-2-pyridyl Me Cl i-Pr Br3-Cl-2-pyridyl Cl Cl i-Pr Br 3-Cl-2-pyridyl Me Br i-Pr Br 3-Cl-2-pyridylCl Br i-Pr Br 3-Cl-2-pyridyl Me H i-Pr Cl 2-Cl-phenyl Cl H i-Pr Cl2-Cl-phenyl Me Cl i-Pr Cl 2-Cl-phenyl Cl Cl i-Pr Cl 2-Cl-phenyl Me Bri-Pr Cl 2-Cl-phenyl Cl Br i-Pr Cl 2-Cl-phenyl Me H i-Pr Cl3-Cl-2-pyridyl Cl H i-Pr Cl 3-Cl-2-pyridyl Me Cl i-Pr Cl 3-Cl-2-pyridylCl Cl i-Pr Cl 3-Cl-2-pyridyl Me Br i-Pr Cl 3-Cl-2-pyridyl Cl Br i-Pr Cl3-Cl-2-pyridyl Me H Me CF₃ 2-Cl-phenyl Cl H Me CF₃ 2-Cl-phenyl Me Cl MeCF₃ 2-Cl-phenyl Cl Cl Me CF₃ 2-Cl-phenyl Me Br Me CF₃ 2-Cl-phenyl Cl BrMe CF₃ 2-Cl-phenyl Me H Me CF₃ 3-Cl-2-pyridyl Cl H Me CF₃ 3-Cl-2-pyridylMe Cl Me CF₃ 3-Cl-2-pyridyl Cl Cl Me CF₃ 3-Cl-2-pyridyl Me Br Me CF₃3-Cl-2-pyridyl Cl Br Me CF₃ 3-Cl-2-pyridyl Me H Me Br 2-Cl-phenyl Cl HMe Br 2-Cl-phenyl Me Cl Me Br 2-Cl-phenyl Cl Cl Me Br 2-Cl-phenyl Me BrMe Br 2-Cl-phenyl Cl Br Me Br 2-Cl-phenyl Me H Me Br 3-Cl-2-pyridyl Cl HMe Br 3-Cl-2-pyridyl Me Cl Me Br 3-Cl-2-pyridyl Cl Cl Me Br3-Cl-2-pyridyl Me Br Me Br 3-Cl-2-pyridyl Cl Br Me Br 3-Cl-2-pyridyl MeH Me Cl 2-Cl-phenyl Cl H Me Cl 2-Cl-phenyl Me Cl Me Cl 2-Cl-phenyl Cl ClMe Cl 2-Cl-phenyl Me Br Me Cl 2-Cl-phenyl Cl Br Me Cl 2-Cl-phenyl Me HMe Cl 3-Cl-2-pyridyl Cl H Me Cl 3-Cl-2-pyridyl Me Cl Me Cl3-Cl-2-pyridyl Cl Cl Me Cl 3-Cl-2-pyridyl Me Br Me Cl 3-Cl-2-pyridyl ClBr Me Cl 3-Cl-2-pyridyl Me H i-Pr OCH₂CF₃ 2-Cl-phenyl Cl H i-Pr OCH₂CF₃2-Cl-phenyl Me Cl i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Cl i-Pr OCH₂CF₃2-Cl-phenyl Me Br i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Br i-Pr OCH₂CF₃2-Cl-phenyl Me H i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl H i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Cl i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Br i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Br i-Pr OCH₂CF₃3-Cl-2-pyridyl Me H i-Pr OCHF₂ 2-Cl-phenyl Cl H i-Pr OCHF₂ 2-Cl-phenylMe Cl i-Pr OCHF₂ 2-Cl-phenyl Cl Cl i-Pr OCHF₂ 2-Cl-phenyl Me Br i-PrOCHF₂ 2-Cl-phenyl Cl Br i-Pr OCHF₂ 2-Cl-phenyl Me H i-Pr OCHF₂3-Cl-2-pyridyl Cl H i-Pr OCHF₂ 3-Cl-2-pyridyl Me Cl i-Pr OCHF₂3-Cl-2-pyridyl Cl Cl i-Pr OCHF₂ 3-Cl-2-pyridyl Me Br i-Pr OCHF₂3-Cl-2-pyridyl Cl Br i-Pr OCHF₂ 3-Cl-2-pyridyl Me H Me OCH₂CF₃2-Cl-phenyl Cl H Me OCH₂CF₃ 2-Cl-phenyl Me Cl Me OCH₂CF₃ 2-Cl-phenyl ClCl Me OCH₂CF₃ 2-Cl-phenyl Me Br Me OCH₂CF₃ 2-Cl-phenyl Cl Br Me OCH₂CF₃2-Cl-phenyl Me H Me OCH₂CF₃ 3-Cl-2-pyridyl Cl H Me OCH₂CF₃3-Cl-2-pyridyl Me Cl Me OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl Me OCH₂CF₃3-Cl-2-pyridyl Me Br Me OCH₂CF₃ 3-Cl-2-pyridyl Cl Br Me OCH₂CF₃3-Cl-2-pyridyl Me H Me OCHF₂ 2-Cl-phenyl Cl H Me OCHF₂ 2-Cl-phenyl Me ClMe OCHF₂ 2-Cl-phenyl Cl Cl Me OCHF₂ 2-Cl-phenyl Me Br Me OCHF₂2-Cl-phenyl Cl Br Me OCHF₂ 2-Cl-phenyl Me H Me OCHF₂ 3-Cl-2-pyridyl Cl HMe OCHF₂ 3-Cl-2-pyridyl Me Cl Me OCHF₂ 3-Cl-2-pyridyl Cl Cl Me OCHF₂3-Cl-2-pyridyl Me Br Me OCHF₂ 3-Cl-2-pyridyl Cl Br Me OCHF₂3-Cl-2-pyridyl GR⁶ is NMe₂ Me H i-Pr CF₃ 2-Cl-phenyl Cl H i-Pr CF₃2-Cl-phenyl Me Cl i-Pr CF₃ 2-Cl-phenyl Cl Cl i-Pr CF₃ 2-Cl-phenyl Me Bri-Pr CF₃ 2-Cl-phenyl Cl Br i-Pr CF₃ 2-Cl-phenyl Me H i-Pr CF₃3-Cl-2-pyridyl Cl H i-Pr CF₃ 3-Cl-2-pyridyl Me Cl i-Pr CF₃3-Cl-2-pyridyl Cl Cl i-Pr CF₃ 3-Cl-2-pyridyl Me Br i-Pr CF₃3-Cl-2-pyridyl Cl Br i-Pr CF₃ 3-Cl-2-pyridyl Me H i-Pr Br 2-Cl-phenyl ClH i-Pr Br 2-Cl-phenyl Me Cl i-Pr Br 2-Cl-phenyl Cl Cl i-Pr Br2-Cl-phenyl Me Br i-Pr Br 2-Cl-phenyl Cl Br i-Pr Br 2-Cl-phenyl Me Hi-Pr Br 3-Cl-2-pyridyl Cl H i-Pr Br 3-Cl-2-pyridyl Me Cl i-Pr Br3-Cl-2-pyridyl Cl Cl i-Pr Br 3-Cl-2-pyridyl Me Br i-Pr Br 3-Cl-2-pyridylCl Br i-Pr Br 3-Cl-2-pyridyl Me H i-Pr Cl 2-Cl-phenyl Cl H i-Pr Cl2-Cl-phenyl Me Cl i-Pr Cl 2-Cl-phenyl Cl Cl i-Pr Cl 2-Cl-phenyl Me Bri-Pr Cl 2-Cl-phenyl Cl Br i-Pr Cl 2-Cl-phenyl Me H i-Pr Cl3-Cl-2-pyridyl Cl H i-Pr Cl 3-Cl-2-pyridyl Me Cl i-Pr Cl 3-Cl-2-pyridylCl Cl i-Pr Cl 3-Cl-2-pyridyl Me Br i-Pr Cl 3-Cl-2-pyridyl Cl Br i-Pr Cl3-Cl-2-pyridyl Me H Me CF₃ 2-Cl-phenyl Cl H Me CF₃ 2-Cl-phenyl Me Cl MeCF₃ 2-Cl-phenyl Cl Cl Me CF₃ 2-Cl-phenyl Me Br Me CF₃ 2-Cl-phenyl Cl BrMe CF₃ 2-Cl-phenyl Me H Me CF₃ 3-Cl-2-pyridyl Cl H Me CF₃ 3-Cl-2-pyridylMe Cl Me CF₃ 3-Cl-2-pyridyl Cl Cl Me CF₃ 3-Cl-2-pyridyl Me Br Me CF₃3-Cl-2-pyridyl Cl Br Me CF₃ 3-Cl-2-pyridyl Me H Me Br 2-Cl-phenyl Cl HMe Br 2-Cl-phenyl Me Cl Me Br 2-Cl-phenyl Cl Cl Me Br 2-Cl-phenyl Me BrMe Br 2-Cl-phenyl Cl Br Me Br 2-Cl-phenyl Me H Me Br 3-Cl-2-pyridyl Cl HMe Br 3-Cl-2-pyridyl Me Cl Me Br 3-Cl-2-pyridyl Cl Cl Me Br3-Cl-2-pyridyl Me Br Me Br 3-Cl-2-pyridyl Cl Br Me Br 3-Cl-2-pyridyl MeH Me Cl 2-Cl-phenyl Cl H Me Cl 2-Cl-phenyl Me Cl Me Cl 2-Cl-phenyl Cl ClMe Cl 2-Cl-phenyl Me Br Me Cl 2-Cl-phenyl Cl Br Me Cl 2-Cl-phenyl Me HMe Cl 3-Cl-2-pyridyl Cl H Me Cl 3-Cl-2-pyridyl Me Cl Me Cl3-Cl-2-pyridyl Cl Cl Me Cl 3-Cl-2-pyridyl Me Br Me Cl 3-Cl-2-pyridyl ClBr Me Cl 3-Cl-2-pyridyl Me H i-Pr OCH₂CF₃ 2-Cl-phenyl Cl H i-Pr OCH₂CF₃2-Cl-phenyl Me Cl i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Cl i-Pr OCH₂CF₃2-Cl-phenyl Me Br i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Br i-Pr OCH₂CF₃2-Cl-phenyl Me H i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl H i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Cl i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Br i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Br i-Pr OCH₂CF₃3-Cl-2-pyridyl Me H i-Pr OCHF₂ 2-Cl-phenyl Cl H i-Pr OCHF₂ 2-Cl-phenylMe Cl i-Pr OCHF₂ 2-Cl-phenyl Cl Cl i-Pr OCHF₂ 2-Cl-phenyl Me Br i-PrOCHF₂ 2-Cl-phenyl Cl Br i-Pr OCHF₂ 2-Cl-phenyl Me H i-Pr OCHF₂3-Cl-2-pyridyl Cl H i-Pr OCHF₂ 3-Cl-2-pyridyl Me Cl i-Pr OCHF₂3-Cl-2-pyridyl Cl Cl i-Pr OCHF₂ 3-Cl-2-pyridyl Me Br i-Pr OCHF₂3-Cl-2-pyridyl Cl Br i-Pr OCHF₂ 3-Cl-2-pyridyl Me H i-Pr Me 2-Cl-phenylCl H i-Pr Me 2-Cl-phenyl Me Cl i-Pr Me 2-Cl-phenyl Cl Cl Me OCH₂CF₃2-Cl-phenyl Me Br Me OCH₂CF₃ 2-Cl-phenyl Cl Br Me OCH₂CF₃ 2-Cl-phenyl MeH Me OCH₂CF₃ 3-Cl-2-pyridyl Cl H Me OCH₂CF₃ 3-Cl-2-pyridyl Me Cl MeOCH₂CF₃ 3-Cl-2-pyridyl Cl Cl Me OCH₂CF₃ 3-Cl-2-pyridyl Me Br Me OCH₂CF₃3-Cl-2-pyridyl Cl Br Me OCH₂CF₃ 3-Cl-2-pyridyl Me H Me OCHF₂ 2-Cl-phenylCl H Me OCHF₂ 2-Cl-phenyl Me Cl Me OCHF₂ 2-Cl-phenyl Cl Cl Me OCHF₂2-Cl-phenyl Me Br Me OCHF₂ 2-Cl-phenyl Cl Br Me OCHF₂ 2-Cl-phenyl Me HMe OCHF₂ 3-Cl-2-pyridyl Cl H Me OCHF₂ 3-Cl-2-pyridyl Me Cl Me OCHF₂3-Cl-2-pyridyl Cl Cl Me OCHF₂ 3-Cl-2-pyridyl Me Br Me OCHF₂3-Cl-2-pyridyl Cl Br Me OCHF₂ 3-Cl-2-pyridyl

TABLE 3

R^(4a) R^(4b) R³ R^(5a) R^(5b) Me H i-Pr Me CF₃ Cl H i-Pr Me CF₃ Me Cli-Pr Me CF₃ Cl Cl i-Pr Me CF₃ Me Br i-Pr Me CF₃ Cl Br i-Pr Me CF₃ Me HMe Me CF₃ Cl H Me Me CF₃ Me Cl Me Me CF₃ Cl Cl Me Me CF₃ Me Br Me Me CF₃Cl Br Me Me CF₃ Me H i-Pr Me OCF₃ Cl H i-Pr Me OCF₃ Me Cl i-Pr Me OCF₃Cl Cl i-Pr Me OCF₃ Me Br i-Pr Me OCF₃ Cl Br i-Pr Me OCF₃ Me H Me Me OCF₃Cl H Me Me OCF₃ Me Cl Me Me OCF₃ Cl Cl Me Me OCF₃ Me Br Me Me OCF₃ Cl BrMe Me OCF₃ Me H i-Pr Me OCH₂CF₃ Cl H i-Pr Me OCH₂CF₃ Me Cl i-Pr MeOCH₂CF₃ Cl Cl i-Pr Me OCH₂CF₃ Me Br i-Pr Me OCH₂CF₃ Cl Br i-Pr MeOCH₂CF₃ Me H Me Me OCH₂CF₃ Cl H Me Me OCH₂CF₃ Me Cl Me Me OCH₂CF₃ Cl ClMe Me OCH₂CF₃ Me Br Me Me OCH₂CF₃ Cl Br Me Me OCH₂CF₃ Me H i-Pr MeCF(CF₃)₂ Cl H i-Pr Me CF(CF₃)₂ Me Cl i-Pr Me CF(CF₃)₂ Cl Cl i-Pr MeCF(CF₃)₂ Me Br i-Pr Me CF(CF₃)₂ Cl Br i-Pr Me CF(CF₃)₂ Me H Me MeCF(CF₃)₂ Cl H Me Me CF(CF₃)₂ Me Cl Me Me CF(CF₃)₂ Cl Cl Me Me CF(CF₃)₂Me Br Me Me CF(CF₃)₂ Cl Br Me Me CF(CF₃)₂

TABLE 4

R^(4a) R^(4b) R³ R^(5a) R^(5b) Me H i-Pr Me CF₃ Cl H i-Pr Me CF₃ Me Cli-Pr Me CF₃ Cl Cl i-Pr Me CF₃ Me Br i-Pr Me CF₃ Cl Br i-Pr Me CF₃ Me HMe Me CF₃ Cl H Me Me CF₃ Me Cl Me Me CF₃ Cl Cl Me Me CF₃ Me Br Me Me CF₃Cl Br Me Me CF₃ Me H i-Pr Me OCF₃ Cl H i-Pr Me OCF₃ Me Cl i-Pr Me OCF₃Cl Cl i-Pr Me OCF₃ Me Br i-Pr Me OCF₃ Cl Br i-Pr Me OCF₃ Me H Me Me OCF₃Cl H Me Me OCF₃ Me Cl Me Me OCF₃ Cl Cl Me Me OCF₃ Me Br Me Me OCF₃ Cl BrMe Me OCF₃ Me H i-Pr Me OCH₂CF₃ Cl H i-Pr Me OCH₂CF₃ Me Cl i-Pr MeOCH₂CF₃ Cl Cl i-Pr Me OCH₂CF₃ Me Br i-Pr Me OCH₂CF₃ Cl Br i-Pr MeOCH₂CF₃ Me H Me Me OCH₂CF₃ Cl H Me Me OCH₂CF₃ Me Cl Me Me OCH₂CF₃ Cl ClMe Me OCH₂CF₃ Me Br Me Me OCH₂CF₃ Cl Br Me Me OCH₂CF₃ Me H i-Pr MeCF(CF₃)₂ Cl H i-Pr Me CF(CF₃)₂ Me Cl i-Pr Me CF(CF₃)₂ Cl Cl i-Pr MeCF(CF₃)₂ Me Br i-Pr Me CF(CF₃)₂ Cl Br i-Pr Me CF(CF₃)₂ Me H Me MeCF(CF₃)₂ Cl H Me Me CF(CF₃)₂ Me Cl Me Me CF(CF₃)₂ Cl Cl Me Me CF(CF₃)₂Me Br Me Me CF(CF₃)₂ Cl Br Me Me CF(CF₃)₂

TABLE 5

R^(4a) R^(4b) R³ R^(5a) R^(5b) Me H i-Pr Me CF₃ Cl H i-Pr Me CF₃ Me Cli-Pr Me CF₃ Cl Cl i-Pr Me CF₃ Me Br i-Pr Me CF₃ Cl Br i-Pr Me CF₃ Me HMe Me CF₃ Cl H Me Me CF₃ Me Cl Me Me CF₃ Cl Cl Me Me CF₃ Me Br Me Me CF₃Cl Br Me Me CF₃ Me H i-Pr Me OCF₃ Cl H i-Pr Me OCF₃ Me Cl i-Pr Me OCF₃Cl Cl i-Pr Me OCF₃ Me Br i-Pr Me OCF₃ Cl Br i-Pr Me OCF₃ Me H Me Me OCF₃Cl H Me Me OCF₃ Me Cl Me Me OCF₃ Cl Cl Me Me OCF₃ Me Br Me Me OCF₃ Cl BrMe Me OCF₃ Me H i-Pr Me OCH₂CF₃ Cl H i-Pr Me OCH₂CF₃ Me Cl i-Pr MeOCH₂CF₃ Cl Cl i-Pr Me OCH₂CF₃ Me Br i-Pr Me OCH₂CF₃ Cl Br i-Pr MeOCH₂CF₃ Me H Me Me OCH₂CF₃ Cl H Me Me OCH₂CF₃ Me Cl Me Me OCH₂CF₃ Cl ClMe Me OCH₂CF₃ Me Br Me Me OCH₂CF₃ Cl Br Me Me OCH₂CF₃ Me H i-Pr MeCF(CF₃)₂ Cl H i-Pr Me CF(CF₃)₂ Me Cl i-Pr Me CF(CF₃)₂ Cl Cl i-Pr MeCF(CF₃)₂ Me Br i-Pr Me CF(CF₃)₂ Cl Br i-Pr Me CF(CF₃)₂ Me H Me MeCF(CF₃)₂ Cl H Me Me CF(CF₃)₂ Me Cl Me Me CF(CF₃)₂ Cl Cl Me Me CF(CF₃)₂Me Br Me Me CF(CF₃)₂ Cl Br Me Me CF(CF₃)₂

TABLE 6

R^(4a) R^(4b) R³ R^(5a) R^(5b) Me H i-Pr CF₃ 2-Cl-phenyl Cl H i-Pr CF₃2-Cl-phenyl Me Cl i-Pr CF₃ 2-Cl-phenyl Cl Cl i-Pr CF₃ 2-Cl-phenyl Me Bri-Pr CF₃ 2-Cl-phenyl Cl Br i-Pr CF₃ 2-Cl-phenyl Me H i-Pr CF₃3-Cl-2-pyridyl Cl H i-Pr CF₃ 3-Cl-2-pyridyl Me Cl i-Pr CF₃3-Cl-2-pyridyl Cl Cl i-Pr CF₃ 3-Cl-2-pyridyl Me Br i-Pr CF₃3-Cl-2-pyridyl Cl Br i-Pr CF₃ 3-Cl-2-pyridyl Me H i-Pr Br 2-Cl-phenyl ClH i-Pr Br 2-Cl-phenyl Me Cl i-Pr Br 2-Cl-phenyl Cl Cl i-Pr Br2-Cl-phenyl Me Br i-Pr Br 2-Cl-phenyl Cl Br i-Pr Br 2-Cl-phenyl Me Hi-Pr Br 3-Cl-2-pyridyl Cl H i-Pr Br 3-Cl-2-pyridyl Me Cl i-Pr Br3-Cl-2-pyridyl Cl Cl i-Pr Br 3-Cl-2-pyridyl Me Br i-Pr Br 3-Cl-2-pyridylCl Br i-Pr Br 3-Cl-2-pyridyl Me H i-Pr Cl 2-Cl-phenyl Cl H i-Pr Cl2-Cl-phenyl Me Cl i-Pr Cl 2-Cl-phenyl Cl Cl i-Pr Cl 2-Cl-phenyl Me Bri-Pr Cl 2-Cl-phenyl Cl Br i-Pr Cl 2-Cl-phenyl Me H i-Pr Cl3-Cl-2-pyridyl Cl H i-Pr Cl 3-Cl-2-pyridyl Me Cl i-Pr Cl 3-Cl-2-pyridylCl Cl i-Pr Cl 3-Cl-2-pyridyl Me Br i-Pr Cl 3-Cl-2-pyridyl Cl Br i-Pr Cl3-Cl-2-pyridyl Me H Me CF₃ 2-Cl-phenyl Cl H Me CF₃ 2-Cl-phenyl Me Cl MeCF₃ 2-Cl-phenyl Cl Cl Me CF₃ 2-Cl-phenyl Me Br Me CF₃ 2-Cl-phenyl Cl BrMe CF₃ 2-Cl-phenyl Me H Me CF₃ 3-Cl-2-pyridyl Cl H Me CF₃ 3-Cl-2-pyridylMe Cl Me CF₃ 3-Cl-2-pyridyl Cl Cl Me CF₃ 3-Cl-2-pyridyl Me Br Me CF₃3-Cl-2-pyridyl Cl Br Me CF₃ 3-Cl-2-pyridyl Me H Me Br 2-Cl-phenyl Cl HMe Br 2-Cl-phenyl Me Cl Me Br 2-Cl-phenyl Cl Cl Me Br 2-Cl-phenyl Me BrMe Br 2-Cl-phenyl Cl Br Me Br 2-Cl-phenyl Me H Me Br 3-Cl-2-pyridyl Cl HMe Br 3-Cl-2-pyridyl Me Cl Me Br 3-Cl-2-pyridyl Cl Cl Me Br3-Cl-2-pyridyl Me Br Me Br 3-Cl-2-pyridyl Cl Br Me Br 3-Cl-2-pyridyl MeH Me Cl 2-Cl-phenyl Cl H Me Cl 2-Cl-phenyl Me Cl Me Cl 2-Cl-phenyl Cl ClMe Cl 2-Cl-phenyl Me Br Me Cl 2-Cl-phenyl Cl Br Me Cl 2-Cl-phenyl Me HMe Cl 3-Cl-2-pyridyl Cl H Me Cl 3-Cl-2-pyridyl Me Cl Me Cl3-Cl-2-pyridyl Cl Cl Me Cl 3-Cl-2-pyridyl Me Br Me Cl 3-Cl-2-pyridyl ClBr Me Cl 3-Cl-2-pyridyl Me H i-Pr OCH₂CF₃ 2-Cl-phenyl Cl H i-Pr OCH₂CF₃2-Cl-phenyl Me Cl i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Cl i-Pr OCH₂CF₃2-Cl-phenyl Me Br i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Br i-Pr OCH₂CF₃2-Cl-phenyl Me H i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl H i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Cl i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Br i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Br i-Pr OCH₂CF₃3-Cl-2-pyridyl Me H i-Pr OCHF₂ 2-Cl-phenyl Cl H i-Pr OCHF₂ 2-Cl-phenylMe Cl i-Pr OCHF₂ 2-Cl-phenyl Cl Cl i-Pr OCHF₂ 2-Cl-phenyl Me Br i-PrOCHF₂ 2-Cl-phenyl Cl Br i-Pr OCHF₂ 2-Cl-phenyl Me H i-Pr OCHF₂3-Cl-2-pyridyl Cl H i-Pr OCHF₂ 3-Cl-2-pyridyl Me Cl i-Pr OCHF₂3-Cl-2-pyridyl Cl Cl i-Pr OCHF₂ 3-Cl-2-pyridyl Me Br i-Pr OCHF₂3-Cl-2-pyridyl Cl Br i-Pr OCHF₂ 3-Cl-2-pyridyl Me H Me OCH₂CF₃2-Cl-phenyl Cl H Me OCH₂CF₃ 2-Cl-phenyl Me Cl Me OCH₂CF₃ 2-Cl-phenyl ClCl Me OCH₂CF₃ 2-Cl-phenyl Me Br Me OCH₂CF₃ 2-Cl-phenyl Cl Br Me OCH₂CF₃2-Cl-phenyl Me H Me OCH₂CF₃ 3-Cl-2-pyridyl Cl H Me OCH₂CF₃3-Cl-2-pyridyl Me Cl Me OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl Me OCH₂CF₃3-Cl-2-pyridyl Me Br Me OCH₂CF₃ 3-Cl-2-pyridyl Cl Br Me OCH₂CF₃3-Cl-2-pyridyl Me H Me OCHF₂ 2-Cl-phenyl Cl H Me OCHF₂ 2-Cl-phenyl Me ClMe OCHF₂ 2-Cl-phenyl Cl Cl Me OCHF₂ 2-Cl-phenyl Me Br Me OCHF₂2-Cl-phenyl Cl Br Me OCHF₂ 2-Cl-phenyl Me H Me OCHF₂ 3-Cl-2-pyridyl Cl HMe OCHF₂ 3-Cl-2-pyridyl Me Cl Me OCHF₂ 3-Cl-2-pyridyl Cl Cl Me OCHF₂3-Cl-2-pyridyl Me Br Me OCHF₂ 3-Cl-2-pyridyl Cl Br Me OCHF₂3-Cl-2-pyridyl Me H i-Pr CF₃ 2-Cl-phenyl Cl H i-Pr CF₃ 2-Cl-phenyl Me Cli-Pr CF₃ 2-Cl-phenyl Cl Cl i-Pr CF₃ 2-Cl-phenyl Me Br i-Pr CF₃2-Cl-phenyl Cl Br i-Pr CF₃ 2-Cl-phenyl Me H i-Pr CF₃ 3-Cl-2-pyridyl Cl Hi-Pr CF₃ 3-Cl-2-pyridyl Me Cl i-Pr CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr CF₃3-Cl-2-pyridyl Me Br i-Pr CF₃ 3-Cl-2-pyridyl Cl Br i-Pr CF₃3-Cl-2-pyridyl Me H i-Pr Br 2-Cl-phenyl Cl H i-Pr Br 2-Cl-phenyl Me Cli-Pr Br 2-Cl-phenyl Cl Cl i-Pr Br 2-Cl-phenyl Me Br i-Pr Br 2-Cl-phenylCl Br i-Pr Br 2-Cl-phenyl Me H i-Pr Br 3-Cl-2-pyridyl Cl H i-Pr Br3-Cl-2-pyridyl Me Cl i-Pr Br 3-Cl-2-pyridyl Cl Cl i-Pr Br 3-Cl-2-pyridylMe Br i-Pr Br 3-Cl-2-pyridyl Cl Br i-Pr Br 3-Cl-2-pyridyl Me H i-Pr Cl2-Cl-phenyl Cl H i-Pr Cl 2-Cl-phenyl Me Cl i-Pr Cl 2-Cl-phenyl Cl Cli-Pr Cl 2-Cl-phenyl Me Br i-Pr Cl 2-Cl-phenyl Cl Br i-Pr Cl 2-Cl-phenylMe H i-Pr Cl 3-Cl-2-pyridyl Cl H i-Pr Cl 3-Cl-2-pyridyl Me Cl i-Pr Cl3-Cl-2-pyridyl Cl Cl i-Pr Cl 3-Cl-2-pyridyl Me Br i-Pr Cl 3-Cl-2-pyridylCl Br i-Pr Cl 3-Cl-2-pyridyl Me H Me CF₃ 2-Cl-phenyl Cl H Me CF₃2-Cl-phenyl Me Cl Me CF₃ 2-Cl-phenyl Cl Cl Me CF₃ 2-Cl-phenyl Me Br MeCF₃ 2-Cl-phenyl Cl Br Me CF₃ 2-Cl-phenyl Me H Me CF₃ 3-Cl-2-pyridyl Cl HMe CF₃ 3-Cl-2-pyridyl Me Cl Me CF₃ 3-Cl-2-pyridyl Cl Cl Me CF₃3-Cl-2-pyridyl Me Br Me CF₃ 3-Cl-2-pyridyl Cl Br Me CF₃ 3-Cl-2-pyridylMe H Me Br 2-Cl-phenyl Cl H Me Br 2-Cl-phenyl Me Cl Me Br 2-Cl-phenyl ClCl Me Br 2-Cl-phenyl Me Br Me Br 2-Cl-phenyl Cl Br Me Br 2-Cl-phenyl MeH Me Br 3-Cl-2-pyridyl Cl H Me Br 3-Cl-2-pyridyl Me Cl Me Br3-Cl-2-pyridyl Cl Cl Me Br 3-Cl-2-pyridyl Me Br Me Br 3-Cl-2-pyridyl ClBr Me Br 3-Cl-2-pyridyl Me H Me Cl 2-Cl-phenyl Cl H Me Cl 2-Cl-phenyl MeCl Me Cl 2-Cl-phenyl Cl Cl Me Cl 2-Cl-phenyl Me Br Me Cl 2-Cl-phenyl ClBr Me Cl 2-Cl-phenyl Me H Me Cl 3-Cl-2-pyridyl Cl H Me Cl 3-Cl-2-pyridylMe Cl Me Cl 3-Cl-2-pyridyl Cl Cl Me Cl 3-Cl-2-pyridyl Me Br Me Cl3-Cl-2-pyridyl Cl Br Me Cl 3-Cl-2-pyridyl Me H i-Pr OCH₂CF₃ 2-Cl-phenylCl H i-Pr OCH₂CF₃ 2-Cl-phenyl Me Cl i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Cl i-PrOCH₂CF₃ 2-Cl-phenyl Me Br i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Br i-Pr OCH₂CF₃2-Cl-phenyl Me H i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl H i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Cl i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Br i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Br i-Pr OCH₂CF₃3-Cl-2-pyridyl Me H i-Pr OCHF₂ 2-Cl-phenyl Cl H i-Pr OCHF₂ 2-Cl-phenylMe Cl i-Pr OCHF₂ 2-Cl-phenyl Cl Cl i-Pr OCHF₂ 2-Cl-phenyl Me Br i-PrOCHF₂ 2-Cl-phenyl Cl Br i-Pr OCHF₂ 2-Cl-phenyl Me H i-Pr OCHF₂3-Cl-2-pyridyl Cl H i-Pr OCHF₂ 3-Cl-2-pyridyl Me Cl i-Pr OCHF₂3-Cl-2-pyridyl Cl Cl i-Pr OCHF₂ 3-Cl-2-pyridyl Me Br i-Pr OCHF₂3-Cl-2-pyridyl Cl Br i-Pr OCHF₂ 3-Cl-2-pyridyl Me H i-Pr Me 2-Cl-phenylCl H i-Pr Me 2-Cl-phenyl Me Cl i-Pr Me 2-Cl-phenyl Cl Cl Me OCH₂CF₃2-Cl-phenyl Me Br Me OCH₂CF₃ 2-Cl-phenyl Cl Br Me OCH₂CF₃ 2-Cl-phenyl MeH Me OCH₂CF₃ 3-Cl-2-pyridyl Cl H Me OCH₂CF₃ 3-Cl-2-pyridyl Me Cl MeOCH₂CF₃ 3-Cl-2-pyridyl Cl Cl Me OCH₂CF₃ 3-Cl-2-pyridyl Me Br Me OCH₂CF₃3-Cl-2-pyridyl Cl Br Me OCH₂CF₃ 3-Cl-2-pyridyl Me H Me OCHF₂ 2-Cl-phenylCl H Me OCHF₂ 2-Cl-phenyl Me Cl Me OCHF₂ 2-Cl-phenyl Cl Cl Me OCHF₂2-Cl-phenyl Me Br Me OCHF₂ 2-Cl-phenyl Cl Br Me OCHF₂ 2-Cl-phenyl Me HMe OCHF₂ 3-Cl-2-pyridyl Cl H Me OCHF₂ 3-Cl-2-pyridyl Me Cl Me OCHF₂3-Cl-2-pyridyl Cl Cl Me OCHF₂ 3-Cl-2-pyridyl Me Br Me OCHF₂3-Cl-2-pyridyl Cl Br Me OCHF₂ 3-Cl-2-pyridyl

TABLE 7

R^(4a) R^(4b) R³ R^(5a) R^(5b) Me H i-Pr CF₃ 2-Cl-phenyl Cl H i-Pr CF₃2-Cl-phenyl Me Cl i-Pr CF₃ 2-Cl-phenyl Cl Cl i-Pr CF₃ 2-Cl-phenyl Me Bri-Pr CF₃ 2-Cl-phenyl Cl Br i-Pr CF₃ 2-Cl-phenyl Me H i-Pr CF₃3-Cl-2-pyridyl Cl H i-Pr CF₃ 3-Cl-2-pyridyl Me Cl i-Pr CF₃3-Cl-2-pyridyl Cl Cl i-Pr CF₃ 3-Cl-2-pyridyl Me Br i-Pr CF₃3-Cl-2-pyridyl Cl Br i-Pr CF₃ 3-Cl-2-pyridyl Me H i-Pr Br 2-Cl-phenyl ClH i-Pr Br 2-Cl-phenyl Me Cl i-Pr Br 2-Cl-phenyl Cl Cl i-Pr Br2-Cl-phenyl Me Br i-Pr Br 2-Cl-phenyl Cl Br i-Pr Br 2-Cl-phenyl Me Hi-Pr Br 3-Cl-2-pyridyl Cl H i-Pr Br 3-Cl-2-pyridyl Me Cl i-Pr Br3-Cl-2-pyridyl Cl Cl i-Pr Br 3-Cl-2-pyridyl Me Br i-Pr Br 3-Cl-2-pyridylCl Br i-Pr Br 3-Cl-2-pyridyl Me H i-Pr Cl 2-Cl-phenyl Cl H i-Pr Cl2-Cl-phenyl Me Cl i-Pr Cl 2-Cl-phenyl Cl Cl i-Pr Cl 2-Cl-phenyl Me Bri-Pr Cl 2-Cl-phenyl Cl Br i-Pr Cl 2-Cl-phenyl Me H i-Pr Cl3-Cl-2-pyridyl Cl H i-Pr Cl 3-Cl-2-pyridyl Me Cl i-Pr Cl 3-Cl-2-pyridylCl Cl i-Pr Cl 3-Cl-2-pyridyl Me Br i-Pr Cl 3-Cl-2-pyridyl Cl Br i-Pr Cl3-Cl-2-pyridyl Me H Me CF₃ 2-Cl-phenyl Cl H Me CF₃ 2-Cl-phenyl Me Cl MeCF₃ 2-Cl-phenyl Cl Cl Me CF₃ 2-Cl-phenyl Me Br Me CF₃ 2-Cl-phenyl Cl BrMe CF₃ 2-Cl-phenyl Me H Me CF₃ 3-Cl-2-pyridyl Cl H Me CF₃ 3-Cl-2-pyridylMe Cl Me CF₃ 3-Cl-2-pyridyl Cl Cl Me CF₃ 3-Cl-2-pyridyl Me Br Me CF₃3-Cl-2-pyridyl Cl Br Me CF₃ 3-Cl-2-pyridyl Me H Me Br 2-Cl-phenyl Cl HMe Br 2-Cl-phenyl Me Cl Me Br 2-Cl-phenyl Cl Cl Me Br 2-Cl-phenyl Me BrMe Br 2-Cl-phenyl Cl Br Me Br 2-Cl-phenyl Me H Me Br 3-Cl-2-pyridyl Cl HMe Br 3-Cl-2-pyridyl Me Cl Me Br 3-Cl-2-pyridyl Cl Cl Me Br3-Cl-2-pyridyl Me Br Me Br 3-Cl-2-pyridyl Cl Br Me Br 3-Cl-2-pyridyl MeH Me Cl 2-Cl-phenyl Cl H Me Cl 2-Cl-phenyl Me Cl Me Cl 2-Cl-phenyl Cl ClMe Cl 2-Cl-phenyl Me Br Me Cl 2-Cl-phenyl Cl Br Me Cl 2-Cl-phenyl Me HMe Cl 3-Cl-2-pyridyl Cl H Me Cl 3-Cl-2-pyridyl Me Cl Me Cl3-Cl-2-pyridyl Cl Cl Me Cl 3-Cl-2-pyridyl Me Br Me Cl 3-Cl-2-pyridyl ClBr Me Cl 3-Cl-2-pyridyl Me H i-Pr OCH₂CF₃ 2-Cl-phenyl Cl H i-Pr OCH₂CF₃2-Cl-phenyl Me Cl i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Cl i-Pr OCH₂CF₃2-Cl-phenyl Me Br i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Br i-Pr OCH₂CF₃2-Cl-phenyl Me H i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl H i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Cl i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Br i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Br i-Pr OCH₂CF₃3-Cl-2-pyridyl Me H i-Pr OCHF₂ 2-Cl-phenyl Cl H i-Pr OCHF₂ 2-Cl-phenylMe Cl i-Pr OCHF₂ 2-Cl-phenyl Cl Cl i-Pr OCHF₂ 2-Cl-phenyl Me Br i-PrOCHF₂ 2-Cl-phenyl Cl Br i-Pr OCHF₂ 2-Cl-phenyl Me H i-Pr OCHF₂2-Cl-2-pyridyl Cl H i-Pr OCHF₂ 3-Cl-2-pyridyl Me Cl i-Pr OCHF₂3-Cl-2-pyridyl Cl Cl i-Pr OCHF₂ 3-Cl-2-pyridyl Me Br i-Pr OCHF₂3-Cl-2-pyridyl Cl Br i-Pr OCHF₂ 3-Cl-2-pyridyl Me H Me OCH₂CF₃2-Cl-phenyl Cl H Me OCH₂CF₃ 2-Cl-phenyl Me Cl Me OCH₂CF₃ 2-Cl-phenyl ClCl Me OCH₂CF₃ 2-Cl-phenyl Me Br Me OCH₂CF₃ 2-Cl-phenyl Cl Br Me OCH₂CF₃2-Cl-phenyl Me H Me OCH₂CF₃ 3-Cl-2-pyridyl Cl H Me OCH₂CF₃3-Cl-2-pyridyl Me Cl Me OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl Me OCH₂CF₃3-Cl-2-pyridyl Me Br Me OCH₂CF₃ 3-Cl-2-pyridyl Cl Br Me OCH₂CF₃3-Cl-2-pyridyl Me H Me OCHF₂ 2-Cl-phenyl Cl H Me OCHF₂ 2-Cl-phenyl Me ClMe OCHF₂ 2-Cl-phenyl Cl Cl Me OCHF₂ 2-Cl-phenyl Me Br Me OCHF₂2-Cl-phenyl Cl Br Me OCHF₂ 2-Cl-phenyl Me H Me OCHF₂ 3-Cl-2-pyridyl Cl HMe OCHF₂ 3-Cl-2-pyridyl Me Cl Me OCHF₂ 3-Cl-2-pyridyl Cl Cl Me OCHF₂3-Cl-2-pyridyl Me Br Me OCHF₂ 3-Cl-2-pyridyl Cl Br Me OCHF₂3-Cl-2-pyridyl Me H i-Pr CF₃ 2-Cl-phenyl Cl H i-Pr CF₃ 2-Cl-phenyl Me Cli-Pr CF₃ 2-Cl-phenyl Cl Cl i-Pr CF₃ 2-Cl-phenyl Me Br i-Pr CF₃2-Cl-phenyl Cl Br i-Pr CF₃ 2-Cl-phenyl Me H i-Pr CF₃ 3-Cl-2-pyridyl Cl Hi-Pr CF₃ 3-Cl-2-pyridyl Me Cl i-Pr CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr CF₃3-Cl-2-pyridyl Me Br i-Pr CF₃ 3-Cl-2-pyridyl Cl Br i-Pr CF₃3-Cl-2-pyridyl Me H i-Pr Br 2-Cl-phenyl Cl H i-Pr Br 2-Cl-phenyl Me Cli-Pr Br 2-Cl-phenyl Cl Cl i-Pr Br 2-Cl-phenyl Me Br i-Pr Br 2-Cl-phenylCl Br i-Pr Br 2-Cl-phenyl Me H i-Pr Br 3-Cl-2-pyridyl Cl H i-Pr Br3-Cl-2-pyridyl Me Cl i-Pr Br 3-Cl-2-pyridyl Cl Cl i-Pr Br 3-Cl-2-pyridylMe Br i-Pr Br 3-Cl-2-pyridyl Cl Br i-Pr Br 3-Cl-2-pyridyl Me H i-Pr Cl2-Cl-phenyl Cl H i-Pr Cl 2-Cl-phenyl Me Cl i-Pr Cl 2-Cl-phenyl Cl Cli-Pr Cl 2-Cl-phenyl Me Br i-Pr Cl 2-Cl-phenyl Cl Br i-Pr Cl 2-Cl-phenylMe H i-Pr Cl 3-Cl-2-pyridyl Cl H i-Pr Cl 3-Cl-2-pyridyl Me Cl i-Pr Cl3-Cl-2-pyridyl Cl Cl i-Pr Cl 3-Cl-2-pyridyl Me Br i-Pr Cl 3-Cl-2-pyridylCl Br i-Pr Cl 3-Cl-2-pyridyl Me H Me CF₃ 2-Cl-phenyl Cl H Me CF₃2-Cl-phenyl Me Cl Me CF₃ 2-Cl-phenyl Cl Cl Me CF₃ 2-Cl-phenyl Me Br MeCF₃ 2-Cl-phenyl Cl Br Me CF₃ 2-Cl-phenyl Me H Me CF₃ 3-Cl-2-pyridyl Cl HMe CF₃ 3-Cl-2-pyridyl Me Cl Me CF₃ 3-Cl-2-pyridyl Cl Cl Me CF₃3-Cl-2-pyridyl Me Br Me CF₃ 3-Cl-2-pyridyl Cl Br Me CF₃ 3-Cl-2-pyridylMe H Me Br 2-Cl-phenyl Cl H Me Br 2-Cl-phenyl Me Cl Me Br 2-Cl-phenyl ClCl Me Br 2-Cl-phenyl Me Br Me Br 2-Cl-phenyl Cl Br Me Br 2-Cl-phenyl MeH Me Br 3-Cl-2-pyridyl Cl H Me Br 3-Cl-2-pyridyl Me Cl Me Br3-Cl-2-pyridyl Cl Cl Me Br 3-Cl-2-pyridyl Me Br Me Br 3-Cl-2-pyridyl ClBr Me Br 3-Cl-2-pyridyl Me H Me Cl 2-Cl-phenyl Cl H Me Cl 2-Cl-phenyl MeCl Me Cl 2-Cl-phenyl Cl Cl Me Cl 2-Cl-phenyl Me Br Me Cl 2-Cl-phenyl ClBr Me Cl 2-Cl-phenyl Me H Me Cl 3-Cl-2-pyridyl Cl H Me Cl 3-Cl-2-pyridylMe Cl Me Cl 3-Cl-2-pyridyl Cl Cl Me Cl 3-Cl-2-pyridyl Me Br Me Cl3-Cl-2-pyridyl Cl Br Me Cl 3-Cl-2-pyridyl Me H i-Pr OCH₂CF₃ 2-Cl-phenylCl H i-Pr OCH₂CF₃ 2-Cl-phenyl Me Cl i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Cl i-PrOCH₂CF₃ 2-Cl-phenyl Me Br i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Br i-Pr OCH₂CF₃2-Cl-phenyl Me H i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl H i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Cl i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Br i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Br i-Pr OCH₂CF₃3-Cl-2-pyridyl Me H i-Pr OCHF₂ 2-Cl-phenyl Cl H i-Pr OCHF₂ 2-Cl-phenylMe Cl i-Pr OCHF₂ 2-Cl-phenyl Cl Cl i-Pr OCHF₂ 2-Cl-phenyl Me Br i-PrOCHF₂ 2-Cl-phenyl Cl Br i-Pr OCHF₂ 2-Cl-phenyl Me H i-Pr OCHF₂3-Cl-2-pyridyl Cl H i-Pr OCHF₂ 3-Cl-2-pyridyl Me Cl i-Pr OCHF₂3-Cl-2-pyridyl Cl Cl i-Pr OCHF₂ 3-Cl-2-pyridyl Me Br i-Pr OCHF₂3-Cl-2-pyridyl Cl Br i-Pr OCHF₂ 3-Cl-2-pyridyl Me H i-Pr Me 2-Cl-phenylCl H i-Pr Me 2-Cl-phenyl Me Cl i-Pr Me 2-Cl-phenyl Cl Cl Me OCH₂CF₃2-Cl-phenyl Me Br Me OCH₂CF₃ 2-Cl-phenyl Cl Br Me OCH₂CF₃ 2-Cl-phenyl MeH Me OCH₂CF₃ 3-Cl-2-pyridyl Cl H Me OCH₂CF₃ 3-Cl-2-pyridyl Me Cl MeOCH₂CF₃ 3-Cl-2-pyridyl Cl Cl Me OCH₂CF₃ 3-Cl-2-pyridyl Me Br Me OCH₂CF₃3-Cl-2-pyridyl Cl Br Me OCH₂CF₃ 3-Cl-2-pyridyl Me H Me OCHF₂ 2-Cl-phenylCl H Me OCHF₂ 2-Cl-phenyl Me Cl Me OCHF₂ 2-Cl-phenyl Cl Cl Me OCHF₂2-Cl-phenyl Me Br Me OCHF₂ 2-Cl-phenyl Cl Br Me OCHF₂ 2-Cl-phenyl Me HMe OCHF₂ 3-Cl-2-pyridyl Cl H Me OCHF₂ 3-Cl-2-pyridyl Me Cl Me OCHF₂3-Cl-2-pyridyl Cl Cl Me OCHF₂ 3-Cl-2-pyridyl Me Br Me OCHF₂3-Cl-2-pyridyl Cl Br Me OCHF₂ 3-Cl-2-pyridyl

TABLE 8

R^(4a) R^(4b) R³ R^(5a) R^(5b) B is NOMe Me H i-Pr CF₃ 2-Cl-phenyl Cl Hi-Pr CF₃ 2-Cl-phenyl Me Cl i-Pr CF₃ 2-Cl-phenyl Cl Cl i-Pr CF₃2-Cl-phenyl Me Br i-Pr CF₃ 2-Cl-phenyl Cl Br i-Pr CF₃ 2-Cl-phenyl Me Hi-Pr CF₃ 3-Cl-2-pyridyl Cl H i-Pr CF₃ 3-Cl-2-pyridyl Me Cl i-Pr CF₃3-Cl-2-pyridyl Cl Cl i-Pr CF₃ 3-Cl-2-pyridyl Me Br i-Pr CF₃3-Cl-2-pyridyl Cl Br i-Pr CF₃ 3-Cl-2-pyridyl Me H i-Pr Br 2-Cl-phenyl ClH i-Pr Br 2-Cl-phenyl Me Cl i-Pr Br 2-Cl-phenyl Cl Cl i-Pr Br2-Cl-phenyl Me Br i-Pr Br 2-Cl-phenyl Cl Br i-Pr Br 2-Cl-phenyl Me Hi-Pr Br 3-Cl-2-pyridyl Cl H i-Pr Br 3-Cl-2-pyridyl Me Cl i-Pr Br3-Cl-2-pyridyl Cl Cl i-Pr Br 3-Cl-2-pyridyl Me Br i-Pr Br 3-Cl-2-pyridylCl Br i-Pr Br 3-Cl-2-pyridyl Me H i-Pr Cl 2-Cl-phenyl Cl H i-Pr Cl2-Cl-phenyl Me Cl i-Pr Cl 2-Cl-phenyl Cl Cl i-Pr Cl 2-Cl-phenyl Me Bri-Pr Cl 2-Cl-phenyl Cl Br i-Pr Cl 2-Cl-phenyl Me H i-Pr Cl3-Cl-2-pyridyl Cl H i-Pr Cl 3-Cl-2-pyridyl Me Cl i-Pr Cl 3-Cl-2-pyridylCl Cl i-Pr Cl 3-Cl-2-pyridyl Me Br i-Pr Cl 3-Cl-2-pyridyl Cl Br i-Pr Cl3-Cl-2-pyridyl Me H Me CF₃ 2-Cl-phenyl Cl H Me CF₃ 2-Cl-phenyl Me Cl MeCF₃ 2-Cl-phenyl Cl Cl Me CF₃ 2-Cl-phenyl Me Br Me CF₃ 2-Cl-phenyl Cl BrMe CF₃ 2-Cl-phenyl Me H Me CF₃ 3-Cl-2-pyridyl Cl H Me CF₃ 3-Cl-2-pyridylMe Cl Me CF₃ 3-Cl-2-pyridyl Cl Cl Me CF₃ 3-Cl-2-pyridyl Me Br Me CF₃3-Cl-2-pyridyl Cl Br Me CF₃ 3-Cl-2-pyridyl Me H Me Br 2-Cl-phenyl Cl HMe Br 2-Cl-phenyl Me Cl Me Br 2-Cl-phenyl Cl Cl Me Br 2-Cl-phenyl Me BrMe Br 2-Cl-phenyl Cl Br Me Br 2-Cl-phenyl Me H Me Br 3-Cl-2-pyridyl Cl HMe Br 3-Cl-2-pyridyl Me Cl Me Br 3-Cl-2-pyridyl Cl Cl Me Br3-Cl-2-pyridyl Me Br Me Br 3-Cl-2-pyridyl Cl Br Me Br 3-Cl-2-pyridyl MeH Me Cl 2-Cl-phenyl Cl H Me Cl 2-Cl-phenyl Me Cl Me Cl 2-Cl-phenyl Cl ClMe Cl 2-Cl-phenyl Me Br Me Cl 2-Cl-phenyl Cl Br Me Cl 2-Cl-phenyl Me HMe Cl 3-Cl-2-pyridyl Cl H Me Cl 3-Cl-2-pyridyl Me Cl Me Cl3-Cl-2-pyridyl Cl Cl Me Cl 3-Cl-2-pyridyl Me Br Me Cl 3-Cl-2-pyridyl ClBr Me Cl 3-Cl-2-pyridyl Me H i-Pr OCH₂CF₃ 2-Cl-phenyl Cl H i-Pr OCH₂CF₃2-Cl-phenyl Me Cl i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Cl i-Pr OCH₂CF₃2-Cl-phenyl Me Br i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Br i-Pr OCH₂CF₃2-Cl-phenyl Me H i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl H i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Cl i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Br i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Br i-Pr OCH₂CF₃3-Cl-2-pyridyl Me H i-Pr OCHF₂ 2-Cl-phenyl Cl H i-Pr OCHF₂ 2-Cl-phenylMe Cl i-Pr OCHF₂ 2-Cl-phenyl Cl Cl i-Pr OCHF₂ 2-Cl-phenyl Me Br i-PrOCHF₂ 2-Cl-phenyl Cl Br i-Pr OCHF₂ 2-Cl-phenyl Me H i-Pr OCHF₂3-Cl-2-pyridyl Cl H i-Pr OCHF₂ 3-Cl-2-pyridyl Me Cl i-Pr OCHF₂3-Cl-2-pyridyl Cl Cl i-Pr OCHF₂ 3-Cl-2-pyridyl Me Br i-Pr OCHF₂3-Cl-2-pyridyl Cl Br i-Pr OCHF₂ 3-Cl-2-pyridyl Me H Me OCH₂CF₃2-Cl-phenyl Cl H Me OCH₂CF₃ 2-Cl-phenyl Me Cl Me OCH₂CF₃ 2-Cl-phenyl ClCl Me OCH₂CF₃ 2-Cl-phenyl Me Br Me OCH₂CF₃ 2-Cl-phenyl Cl Br Me OCH₂CF₃2-Cl-phenyl Me H Me OCH₂CF₃ 3-Cl-2-pyridyl Cl H Me OCH₂CF₃3-Cl-2-pyridyl Me Cl Me OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl Me OCH₂CF₃3-Cl-2-pyridyl Me Br Me OCH₂CF₃ 3-Cl-2-pyridyl Cl Br Me OCH₂CF₃3-Cl-2-pyridyl Me H Me OCHF₂ 2-Cl-phenyl Cl H Me OCHF₂ 2-Cl-phenyl Me ClMe OCHF₂ 2-Cl-phenyl Cl Cl Me OCHF₂ 2-Cl-phenyl Me Br Me OCHF₂2-Cl-phenyl Cl Br Me OCHF₂ 2-Cl-phenyl Me H Me OCHF₂ 3-Cl-2-pyridyl Cl HMe OCHF₂ 3-Cl-2-pyridyl Me Cl Me OCHF₂ 3-Cl-2-pyridyl Cl Cl Me OCHF₂3-Cl-2-pyridyl Me Br Me OCHF₂ 3-Cl-2-pyridyl Cl Br Me OCHF₂3-Cl-2-pyridyl B is NNMe₂ Me H i-Pr CF₃ 2-Cl-phenyl Cl H i-Pr CF₃2-Cl-phenyl Me Cl i-Pr CF₃ 2-Cl-phenyl Cl Cl i-Pr CF₃ 2-Cl-phenyl Me Bri-Pr CF₃ 2-Cl-phenyl Cl Br i-Pr CF₃ 2-Cl-phenyl Me H i-Pr CF₃3-Cl-2-pyridyl Cl H i-Pr CF₃ 3-Cl-2-pyridyl Me Cl i-Pr CF₃3-Cl-2-pyridyl Cl Cl i-Pr CF₃ 3-Cl-2-pyridyl Me Br i-Pr CF₃3-Cl-2-pyridyl Cl Br i-Pr CF₃ 3-Cl-2-pyridyl Me H i-Pr Br 2-Cl-phenyl ClH i-Pr Br 2-Cl-phenyl Me Cl i-Pr Br 2-Cl-phenyl Cl Cl i-Pr Br2-Cl-phenyl Me Br i-Pr Br 2-Cl-phenyl Cl Br i-Pr Br 2-Cl-phenyl Me Hi-Pr Br 3-Cl-2-pyridyl Cl H i-Pr Br 3-Cl-2-pyridyl Me Cl i-Pr Br3-Cl-2-pyridyl Cl Cl i-Pr Br 3-Cl-2-pyridyl Me Br i-Pr Br 3-Cl-2-pyridylCl Br i-Pr Br 3-Cl-2-pyridyl Me H i-Pr Cl 2-Cl-phenyl Cl H i-Pr Cl2-Cl-phenyl Me Cl i-Pr Cl 2-Cl-phenyl Cl Cl i-Pr Cl 2-Cl-phenyl Me Bri-Pr Cl 2-Cl-phenyl Cl Br i-Pr Cl 2-Cl-phenyl Me H i-Pr Cl3-Cl-2-pyridyl Cl H i-Pr Cl 3-Cl-2-pyridyl Me Cl i-Pr Cl 3-Cl-2-pyridylCl Cl i-Pr Cl 3-Cl-2-pyridyl Me Br i-Pr Cl 3-Cl-2-pyridyl Cl Br i-Pr Cl3-Cl-2-pyridyl Me H Me CF₃ 2-Cl-phenyl Cl H Me CF₃ 2-Cl-phenyl Me Cl MeCF₃ 2-Cl-phenyl Cl Cl Me CF₃ 2-Cl-phenyl Me Br Me CF₃ 2-Cl-phenyl Cl BrMe CF₃ 2-Cl-phenyl Me H Me CF₃ 3-Cl-2-pyridyl Cl H Me CF₃ 3-Cl-2-pyridylMe Cl Me CF₃ 3-Cl-2-pyridyl Cl Cl Me CF₃ 3-Cl-2-pyridyl Me Br Me CF₃3-Cl-2-pyridyl Cl Br Me CF₃ 3-Cl-2-pyridyl Me H Me Br 2-Cl-phenyl Cl HMe Br 2-Cl-phenyl Me Cl Me Br 2-Cl-phenyl Cl Cl Me Br 2-Cl-phenyl Me BrMe Br 2-Cl-phenyl Cl Br Me Br 2-Cl-phenyl Me H Me Br 3-Cl-2-pyridyl Cl HMe Br 3-Cl-2-pyridyl Me Cl Me Br 3-Cl-2-pyridyl Cl Cl Me Br3-Cl-2-pyridyl Me Br Me Br 3-Cl-2-pyridyl Cl Br Me Br 3-Cl-2-pyridyl MeH Me Cl 2-Cl-phenyl Cl H Me Cl 2-Cl-phenyl Me Cl Me Cl 2-Cl-phenyl Cl ClMe Cl 2-Cl-phenyl Me Br Me Cl 2-Cl-phenyl Cl Br Me Cl 2-Cl-phenyl Me HMe Cl 3-Cl-2-pyridyl Cl H Me Cl 3-Cl-2-pyridyl Me Cl Me Cl3-Cl-2-pyridyl Cl Cl Me Cl 3-Cl-2-pyridyl Me Br Me Cl 3-Cl-2-pyridyl ClBr Me Cl 3-Cl-2-pyridyl Me H i-Pr OCH₂CF₃ 2-Cl-phenyl Cl H i-Pr OCH₂CF₃2-Cl-phenyl Me Cl i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Cl i-Pr OCH₂CF₃2-Cl-phenyl Me Br i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Br i-Pr OCH₂CF₃2-Cl-phenyl Me H i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl H i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Cl i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Br i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Br i-Pr OCH₂CF₃3-Cl-2-pyridyl Me H i-Pr OCHF₂ 2-Cl-phenyl Cl H i-Pr OCHF₂ 2-Cl-phenylMe Cl i-Pr OCHF₂ 2-Cl-phenyl Cl Cl i-Pr OCHF₂ 2-Cl-phenyl Me Br i-PrOCHF₂ 2-Cl-phenyl Cl Br i-Pr OCHF₂ 2-Cl-phenyl Me H i-Pr OCHF₂3-Cl-2-pyridyl Cl H i-Pr OCHF₂ 3-Cl-2-pyridyl Me Cl i-Pr OCHF₂3-Cl-2-pyridyl Cl Cl i-Pr OCHF₂ 3-Cl-2-pyridyl Me Br i-Pr OCHF₂3-Cl-2-pyridyl Cl Br i-Pr OCHF₂ 3-Cl-2-pyridyl Me H i-Pr Me 2-Cl-phenylCl H i-Pr Me 2-Cl-phenyl Me Cl i-Pr Me 2-Cl-phenyl Cl Cl Me OCH₂CF₃2-Cl-phenyl Me Br Me OCH₂CF₃ 2-Cl-phenyl Cl Br Me OCH₂CF₃ 2-Cl-phenyl MeH Me OCH₂CF₃ 3-Cl-2-pyridyl Cl H Me OCH₂CF₃ 3-Cl-2-pyridyl Me Cl MeOCH₂CF₃ 3-Cl-2-pyridyl Cl Cl Me OCH₂CF₃ 3-Cl-2-pyridyl Me Br Me OCH₂CF₃3-Cl-2-pyridyl Cl Br Me OCH₂CF₃ 3-Cl-2-pyridyl Me H Me OCHF₂ 2-Cl-phenylCl H Me OCHF₂ 2-Cl-phenyl Me Cl Me OCHF₂ 2-Cl-phenyl Cl Cl Me OCHF₂2-Cl-phenyl Me Br Me OCHF₂ 2-Cl-phenyl Cl Br Me OCHF₂ 2-Cl-phenyl Me HMe OCHF₂ 3-Cl-2-pyridyl Cl H Me OCHF₂ 3-Cl-2-pyridyl Me Cl Me OCHF₂3-Cl-2-pyridyl Cl Cl Me OCHF₂ 3-Cl-2-pyridyl Me Br Me OCHF₂3-Cl-2-pyridyl Cl Br Me OCHF₂ 3-Cl-2-pyridyl B is S═O Me H i-Pr CF₃2-Cl-phenyl Cl H i-Pr CF₃ 2-Cl-phenyl Me Cl i-Pr CF₃ 2-Cl-phenyl Cl Cli-Pr CF₃ 2-Cl-phenyl Me Br i-Pr CF₃ 2-Cl-phenyl Cl Br i-Pr CF₃2-Cl-phenyl Me H i-Pr CF₃ 3-Cl-2-pyridyl Cl H i-Pr CF₃ 3-Cl-2-pyridyl MeCl i-Pr CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr CF₃ 3-Cl-2-pyridyl Me Br i-Pr CF₃3-Cl-2-pyridyl Cl Br i-Pr CF₃ 3-Cl-2-pyridyl Me H i-Pr Br 2-Cl-phenyl ClH i-Pr Br 2-Cl-phenyl Me Cl i-Pr Br 2-Cl-phenyl Cl Cl i-Pr Br2-Cl-phenyl Me Br i-Pr Br 2-Cl-phenyl Cl Br i-Pr Br 2-Cl-phenyl Me Hi-Pr Br 3-Cl-2-pyridyl Cl H i-Pr Br 3-Cl-2-pyridyl Me Cl i-Pr Br3-Cl-2-pyridyl Cl Cl i-Pr Br 3-Cl-2-pyridyl Me Br i-Pr Br 3-Cl-2-pyridylCl Br i-Pr Br 3-Cl-2-pyridyl Me H i-Pr Cl 2-Cl-phenyl Cl H i-Pr Cl2-Cl-phenyl Me Cl i-Pr Cl 2-Cl-phenyl Cl Cl i-Pr Cl 2-Cl-phenyl Me Bri-Pr Cl 2-Cl-phenyl Cl Br i-Pr Cl 2-Cl-phenyl Me H i-Pr Cl3-Cl-2-pyridyl Cl H i-Pr Cl 3-Cl-2-pyridyl Me Cl i-Pr Cl 3-Cl-2-pyridylCl Cl i-Pr Cl 3-Cl-2-pyridyl Me Br i-Pr Cl 3-Cl-2-pyridyl Cl Br i-Pr Cl3-Cl-2-pyridyl Me H Me CF₃ 2-Cl-phenyl Cl H Me CF₃ 2-Cl-phenyl Me Cl MeCF₃ 2-Cl-phenyl Cl Cl Me CF₃ 2-Cl-phenyl Me Br Me CF₃ 2-Cl-phenyl Cl BrMe CF₃ 2-Cl-phenyl Me H Me CF₃ 3-Cl-2-pyridyl Cl H Me CF₃ 3-Cl-2-pyridylMe Cl Me CF₃ 3-Cl-2-pyridyl Cl Cl Me CF₃ 3-Cl-2-pyridyl Me Br Me CF₃3-Cl-2-pyridyl Cl Br Me CF₃ 3-Cl-2-pyridyl Me H Me Br 2-Cl-phenyl Cl HMe Br 2-Cl-phenyl Me Cl Me Br 2-Cl-phenyl Cl Cl Me Br 2-Cl-phenyl Me BrMe Br 2-Cl-phenyl Cl Br Me Br 2-Cl-phenyl Me H Me Br 3-Cl-2-pyridyl Cl HMe Br 3-Cl-2-pyridyl Me Cl Me Br 3-Cl-2-pyridyl Cl Cl Me Br3-Cl-2-pyridyl Me Br Me Br 3-Cl-2-pyridyl Cl Br Me Br 3-Cl-2-pyridyl MeH Me Cl 2-Cl-phenyl Cl H Me Cl 2-Cl-phenyl Me Cl Me Cl 2-Cl-phenyl Cl ClMe Cl 2-Cl-phenyl Me Br Me Cl 2-Cl-phenyl Cl Br Me Cl 2-Cl-phenyl Me HMe Cl 3-Cl-2-pyridyl Cl H Me Cl 3-Cl-2-pyridyl Me Cl Me Cl3-Cl-2-pyridyl Cl Cl Me Cl 3-Cl-2-pyridyl Me Br Me Cl 3-Cl-2-pyridyl ClBr Me Cl 3-Cl-2-pyridyl Me H i-Pr OCH₂CF₃ 2-Cl-phenyl Cl H i-Pr OCH₂CF₃2-Cl-phenyl Me Cl i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Cl i-Pr OCH₂CF₃2-Cl-phenyl Me Br i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Br i-Pr OCH₂CF₃2-Cl-phenyl Me H i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl H i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Cl i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Br i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Br i-Pr OCH₂CF₃3-Cl-2-pyridyl Me H i-Pr OCHF₂ 2-Cl-phenyl Cl H i-Pr OCHF₂ 2-Cl-phenylMe Cl i-Pr OCHF₂ 2-Cl-phenyl Cl Cl i-Pr OCHF₂ 2-Cl-phenyl Me Br i-PrOCHF₂ 2-Cl-phenyl Cl Br i-Pr OCHF₂ 2-Cl-phenyl Me H i-Pr OCHF₂3-Cl-2-pyridyl Cl H i-Pr OCHF₂ 3-Cl-2-pyridyl Me Cl i-Pr OCHF₂3-Cl-2-pyridyl Cl Cl i-Pr OCHF₂ 3-Cl-2-pyridyl Me Br i-Pr OCHF₂3-Cl-2-pyridyl Cl Br i-Pr OCHF₂ 3-Cl-2-pyridyl Me H Me OCH₂CF₃2-Cl-phenyl Cl H Me OCH₂CF₃ 2-Cl-phenyl Me Cl Me OCH₂CF₃ 2-Cl-phenyl ClCl Me OCH₂CF₃ 2-Cl-phenyl Me Br Me OCH₂CF₃ 2-Cl-phenyl Cl Br Me OCH₂CF₃2-Cl-phenyl Me H Me OCH₂CF₃ 3-Cl-2-pyridyl Cl H Me OCH₂CF₃3-Cl-2-pyridyl Me Cl Me OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl Me OCH₂CF₃3-Cl-2-pyridyl Me Br Me OCH₂CF₃ 3-Cl-2-pyridyl Cl Br Me OCH₂CF₃3-Cl-2-pyridyl Me H Me OCHF₂ 2-Cl-phenyl Cl H Me OCHF₂ 2-Cl-phenyl Me ClMe OCHF₂ 2-Cl-phenyl Cl Cl Me OCHF₂ 2-Cl-phenyl Me Br Me OCHF₂2-Cl-phenyl Cl Br Me OCHF₂ 2-Cl-phenyl Me H Me OCHF₂ 3-Cl-2-pyridyl Cl HMe OCHF₂ 3-Cl-2-pyridyl Me Cl Me OCHF₂ 3-Cl-2-pyridyl Cl Cl Me OCHF₂3-Cl-2-pyridyl Me Br Me OCHF₂ 3-Cl-2-pyridyl Cl Br Me OCHF₂3-Cl-2-pyridyl B is N—CN Me H i-Pr CF₃ 2-Cl-phenyl Cl H i-Pr CF₃2-Cl-phenyl Me Cl i-Pr CF₃ 2-Cl-phenyl Cl Cl i-Pr CF₃ 2-Cl-phenyl Me Bri-Pr CF₃ 2-Cl-phenyl Cl Br i-Pr CF₃ 2-Cl-phenyl Me H i-Pr CF₃3-Cl-2-pyridyl Cl H i-Pr CF₃ 3-Cl-2-pyridyl Me Cl i-Pr CF₃3-Cl-2-pyridyl Cl Cl i-Pr CF₃ 3-Cl-2-pyridyl Me Br i-Pr CF₃3-Cl-2-pyridyl Cl Br i-Pr CF₃ 3-Cl-2-pyridyl Me H i-Pr Br 2-Cl-phenyl ClH i-Pr Br 2-Cl-phenyl Me Cl i-Pr Br 2-Cl-phenyl Cl Cl i-Pr Br2-Cl-phenyl Me Br i-Pr Br 2-Cl-phenyl Cl Br i-Pr Br 2-Cl-phenyl Me Hi-Pr Br 3-Cl-2-pyridyl Cl H i-Pr Br 3-Cl-2-pyridyl Me Cl i-Pr Br3-Cl-2-pyridyl Cl Cl i-Pr Br 3-Cl-2-pyridyl Me Br i-Pr Br 3-Cl-2-pyridylCl Br i-Pr Br 3-Cl-2-pyridyl Me H i-Pr Cl 2-Cl-phenyl Cl H i-Pr Cl2-Cl-phenyl Me Cl i-Pr Cl 2-Cl-phenyl Cl Cl i-Pr Cl 2-Cl-phenyl Me Bri-Pr Cl 2-Cl-phenyl Cl Br i-Pr Cl 2-Cl-phenyl Me H i-Pr Cl3-Cl-2-pyridyl Cl H i-Pr Cl 3-Cl-2-pyridyl Me Cl i-Pr Cl 3-Cl-2-pyridylCl Cl i-Pr Cl 3-Cl-2-pyridyl Me Br i-Pr Cl 3-Cl-2-pyridyl Cl Br i-Pr Cl3-Cl-2-pyridyl Me H Me CF₃ 2-Cl-phenyl Cl H Me CF₃ 2-Cl-phenyl Me Cl MeCF₃ 2-Cl-phenyl Cl Cl Me CF₃ 2-Cl-phenyl Me Br Me CF₃ 2-Cl-phenyl Cl BrMe CF₃ 2-Cl-phenyl Me H Me CF₃ 3-Cl-2-pyridyl Cl H Me CF₃ 3-Cl-2-pyridylMe Cl Me CF₃ 3-Cl-2-pyridyl Cl Cl Me CF₃ 3-Cl-2-pyridyl Me Br Me CF₃3-Cl-2-pyridyl Cl Br Me CF₃ 3-Cl-2-pyridyl Me H Me Br 2-Cl-phenyl Cl HMe Br 2-Cl-phenyl Me Cl Me Br 2-Cl-phenyl Cl Cl Me Br 2-Cl-phenyl Me BrMe Br 2-Cl-phenyl Cl Br Me Br 2-Cl-phenyl Me H Me Br 3-Cl-2-pyridyl Cl HMe Br 3-Cl-2-pyridyl Me Cl Me Br 3-Cl-2-pyridyl Cl Cl Me Br3-Cl-2-pyridyl Me Br Me Br 3-Cl-2-pyridyl Cl Br Me Br 3-Cl-2-pyridyl MeH Me Cl 2-Cl-phenyl Cl H Me Cl 2-Cl-phenyl Me Cl Me Cl 2-Cl-phenyl Cl ClMe Cl 2-Cl-phenyl Me Br Me Cl 2-Cl-phenyl Cl Br Me Cl 2-Cl-phenyl Me HMe Cl 3-Cl-2-pyridyl Cl H Me Cl 3-Cl-2-pyridyl Me Cl Me Cl3-Cl-2-pyridyl Cl Cl Me Cl 3-Cl-2-pyridyl Me Br Me Cl 3-Cl-2-pyridyl ClBr Me Cl 3-Cl-2-pyridyl Me H i-Pr OCH₂CF₃ 2-Cl-phenyl Cl H i-Pr OCH₂CF₃2-Cl-phenyl Me Cl i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Cl i-Pr OCH₂CF₃2-Cl-phenyl Me Br i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Br i-Pr OCH₂CF₃2-Cl-phenyl Me H i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl H i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Cl i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Br i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Br i-Pr OCH₂CF₃3-Cl-2-pyridyl Me H i-Pr OCHF₂ 2-Cl-phenyl Cl H i-Pr OCHF₂ 2-Cl-phenylMe Cl i-Pr OCHF₂ 2-Cl-phenyl Cl Cl i-Pr OCHF₂ 2-Cl-phenyl Me Br i-PrOCHF₂ 2-Cl-phenyl Cl Br i-Pr OCHF₂ 2-Cl-phenyl Me H i-Pr OCHF₂3-Cl-2-pyridyl Cl H i-Pr OCHF₂ 3-Cl-2-pyridyl Me Cl i-Pr OCHF₂3-Cl-2-pyridyl Cl Cl i-Pr OCHF₂ 3-Cl-2-pyridyl Me Br i-Pr OCHF₂3-Cl-2-pyridyl Cl Br i-Pr OCHF₂ 3-Cl-2-pyridyl Me H i-Pr Me 2-Cl-phenylCl H i-Pr Me 2-Cl-phenyl Me Cl i-Pr Me 2-Cl-phenyl Cl Cl Me OCH₂CF₃2-Cl-phenyl Me Br Me OCH₂CF₃ 2-Cl-phenyl Cl Br Me OCH₂CF₃ 2-Cl-phenyl MeH Me OCH₂CF₃ 3-Cl-2-pyridyl Cl H Me OCH₂CF₃ 3-Cl-2-pyridyl Me Cl MeOCH₂CF₃ 3-Cl-2-pyridyl Cl Cl Me OCH₂CF₃ 3-Cl-2-pyridyl Me Br Me OCH₂CF₃3-Cl-2-pyridyl Cl Br Me OCH₂CF₃ 3-Cl-2-pyridyl Me H Me OCHF₂ 2-Cl-phenylCl H Me OCHF₂ 2-Cl-phenyl Me Cl Me OCHF₂ 2-Cl-phenyl Cl Cl Me OCHF₂2-Cl-phenyl Me Br Me OCHF₂ 2-Cl-phenyl Cl Br Me OCHF₂ 2-Cl-phenyl Me HMe OCHF₂ 3-Cl-2-pyridyl Cl H Me OCHF₂ 3-Cl-2-pyridyl Me Cl Me OCHF₂3-Cl-2-pyridyl Cl Cl Me OCHF₂ 3-Cl-2-pyridyl Me Br Me OCHF₂3-Cl-2-pyridyl Cl Br Me OCHF₂ 3-Cl-2-pyridyl B is N—NO₂ Me H i-Pr CF₃2-Cl-phenyl Cl H i-Pr CF₃ 2-Cl-phenyl Me Cl i-Pr CF₃ 2-Cl-phenyl Cl Cli-Pr CF₃ 2-Cl-phenyl Me Br i-Pr CF₃ 2-Cl-phenyl Cl Br i-Pr CF₃2-Cl-phenyl Me H i-Pr CF₃ 3-Cl-2-pyridyl Cl H i-Pr CF₃ 3-Cl-2-pyridyl MeCl i-Pr CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr CF₃ 3-Cl-2-pyridyl Me Br i-Pr CF₃3-Cl-2-pyridyl Cl Br i-Pr CF₃ 3-Cl-2-pyridyl Me H i-Pr Br 2-Cl-phenyl ClH i-Pr Br 2-Cl-phenyl Me Cl i-Pr Br 2-Cl-phenyl Cl Cl i-Pr Br2-Cl-phenyl Me Br i-Pr Br 2-Cl-phenyl Cl Br i-Pr Br 2-Cl-phenyl Me Hi-Pr Br 3-Cl-2-pyridyl Cl H i-Pr Br 3-Cl-2-pyridyl Me Cl i-Pr Br3-Cl-2-pyridyl Cl Cl i-Pr Br 3-Cl-2-pyridyl Me Br i-Pr Br 3-Cl-2-pyridylCl Br i-Pr Br 3-Cl-2-pyridyl Me H i-Pr Cl 2-Cl-phenyl Cl H i-Pr Cl2-Cl-phenyl Me Cl i-Pr Cl 2-Cl-phenyl Cl Cl i-Pr Cl 2-Cl-phenyl Me Bri-Pr Cl 2-Cl-phenyl Cl Br i-Pr Cl 2-Cl-phenyl Me H i-Pr Cl3-Cl-2-pyridyl Cl H i-Pr Cl 3-Cl-2-pyridyl Me Cl i-Pr Cl 3-Cl-2-pyridylCl Cl i-Pr Cl 3-Cl-2-pyridyl Me Br i-Pr Cl 3-Cl-2-pyridyl Cl Br i-Pr Cl3-Cl-2-pyridyl Me H Me CF₃ 2-Cl-phenyl Cl H Me CF₃ 2-Cl-phenyl Me Cl MeCF₃ 2-Cl-phenyl Cl Cl Me CF₃ 2-Cl-phenyl Me Br Me CF₃ 2-Cl-phenyl Cl BrMe CF₃ 2-Cl-phenyl Me H Me CF₃ 3-Cl-2-pyridyl Cl H Me CF₃ 3-Cl-2-pyridylMe Cl Me CF₃ 3-Cl-2-pyridyl Cl Cl Me CF₃ 3-Cl-2-pyridyl Me Br Me CF₃3-Cl-2-pyridyl Cl Br Me CF₃ 3-Cl-2-pyridyl Me H Me Br 2-Cl-phenyl Cl HMe Br 2-Cl-phenyl Me Cl Me Br 2-Cl-phenyl Cl Cl Me Br 2-Cl-phenyl Me BrMe Br 2-Cl-phenyl Cl Br Me Br 2-Cl-phenyl Me H Me Br 3-Cl-2-pyridyl Cl HMe Br 3-Cl-2-pyridyl Me Cl Me Br 3-Cl-2-pyridyl Cl Cl Me Br3-Cl-2-pyridyl Me Br Me Br 3-Cl-2-pyridyl Cl Br Me Br 3-Cl-2-pyridyl MeH Me Cl 2-Cl-phenyl Cl H Me Cl 2-Cl-phenyl Me Cl Me Cl 2-Cl-phenyl Cl ClMe Cl 2-Cl-phenyl Me Br Me Cl 2-Cl-phenyl Cl Br Me Cl 2-Cl-phenyl Me HMe Cl 3-Cl-2-pyridyl Cl H Me Cl 3-Cl-2-pyridyl Me Cl Me Cl3-CJ-2-pyridyl Cl Cl Me Cl 3-Cl-2-pyridyl Me Br Me Cl 3-Cl-2-pyridyl ClBr Me Cl 3-Cl-2-pyridyl Me H i-Pr OCH₂CF₃ 2-Cl-phenyl Cl H i-Pr OCH₂CF₃2-Cl-phenyl Me Cl i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Cl i-Pr OCH₂CF₃2-Cl-phenyl Me Br i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Br i-Pr OCH₂CF₃2-Cl-phenyl Me H i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl H i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Cl i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Br i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Br i-Pr OCH₂CF₃3-Cl-2-pyridyl Me H i-Pr OCHF₂ 2-Cl-phenyl Cl H i-Pr OCHF₂ 2-Cl-phenylMe Cl i-Pr OCHF₂ 2-Cl-phenyl Cl Cl i-Pr OCHF₂ 2-Cl-phenyl Me Br i-PrOCHF₂ 2-Cl-phenyl Cl Br i-Pr OCHF₂ 2-Cl-phenyl Me H i-Pr OCHF₂3-Cl-2-pyridyl Cl H i-Pr OCHF₂ 3-Cl-2-pyridyl Me Cl i-Pr OCHF₂3-Cl-2-pyridyl Cl Cl i-Pr OCHF₂ 3-Cl-2-pyridyl Me Br i-Pr OCHF₂3-Cl-2-pyridyl Cl Br i-Pr OCHF₂ 3-Cl-2-pyridyl Me H Me OCH₂CF₃2-Cl-phenyl Cl H Me OCH₂CF₃ 2-Cl-phenyl Me Cl Me OCH₂CF₃ 2-Cl-phenyl ClCl Me OCH₂CF₃ 2-Cl-phenyl Me Br Me OCH₂CF₃ 2-Cl-phenyl Cl Br Me OCH₂CF₃2-Cl-phenyl Me H Me OCH₂CF₃ 3-Cl-2-pyridyl Cl H Me OCH₂CF₃3-Cl-2-pyridyl Me Cl Me OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl Me OCH₂CF₃3-Cl-2-pyridyl Me Br Me OCH₂CF₃ 3-Cl-2-pyridyl Cl Br Me OCH₂CF₃3-Cl-2-pyridyl Me H Me OCHF₂ 2-Cl-phenyl Cl H Me OCHF₂ 2-Cl-phenyl Me ClMe OCHF₂ 2-Cl-phenyl Cl Cl Me OCHF₂ 2-Cl-phenyl Me Br Me OCHF₂2-Cl-phenyl Cl Br Me OCHF₂ 2-Cl-phenyl Me H Me OCHF₂ 3-Cl-2-pyridyl Cl HMe OCHF₂ 3-Cl-2-pyridyl Me Cl Me OCHF₂ 3-Cl-2-pyridyl Cl Cl Me OCHF₂3-Cl-2-pyridyl Me Br Me OCHF₂ 3-Cl-2-pyridyl Cl Br Me OCHF₂3-Cl-2-pyridyl B is NMe Me H i-Pr CF₃ 2-Cl-phenyl Cl H i-Pr CF₃2-Cl-phenyl Me Cl i-Pr CF₃ 2-Cl-phenyl Cl Cl i-Pr CF₃ 2-Cl-phenyl Me Bri-Pr CF₃ 2-Cl-phenyl Cl Br i-Pr CF₃ 2-Cl-phenyl Me H i-Pr CF₃3-Cl-2-pyridyl Cl H i-Pr CF₃ 3-Cl-2-pyridyl Me Cl i-Pr CF₃3-Cl-2-pyridyl Cl Cl i-Pr CF₃ 3-Cl-2-pyridyl Me Br i-Pr CF₃3-Cl-2-pyridyl Cl Br i-Pr CF₃ 3-Cl-2-pyridyl Me H i-Pr Br 2-Cl-phenyl ClH i-Pr Br 2-Cl-phenyl Me Cl i-Pr Br 2-Cl-phenyl Cl Cl i-Pr Br2-Cl-phenyl Me Br i-Pr Br 2-Cl-phenyl Cl Br i-Pr Br 2-Cl-phenyl Me Hi-Pr Br 3-Cl-2-pyridyl Cl H i-Pr Br 3-Cl-2-pyridyl Me Cl i-Pr Br3-Cl-2-pyridyl Cl Cl i-Pr Br 3-Cl-2-pyridyl Me Br i-Pr Br 3-Cl-2-pyridylCl Br i-Pr Br 3-Cl-2-pyridyl Me H i-Pr Cl 2-Cl-phenyl Cl H i-Pr Cl2-Cl-phenyl Me Cl i-Pr Cl 2-Cl-phenyl Cl Cl i-Pr Cl 2-Cl-phenyl Me Bri-Pr Cl 2-Cl-phenyl Cl Br i-Pr Cl 2-Cl-phenyl Me H i-Pr Cl3-Cl-2-pyridyl Cl H i-Pr Cl 3-Cl-2-pyridyl Me Cl i-Pr Cl 3-Cl-2-pyridylCl Cl i-Pr Cl 3-Cl-2-pyridyl Me Br i-Pr Cl 3-Cl-2-pyridyl Cl Br i-Pr Cl3-Cl-2-pyridyl Me H Me CF₃ 2-Cl-phenyl Cl H Me CF₃ 2-Cl-phenyl Me Cl MeCF₃ 2-Cl-phenyl Cl Cl Me CF₃ 2-Cl-phenyl Me Br Me CF₃ 2-Cl-phenyl Cl BrMe CF₃ 2-Cl-phenyl Me H Me CF₃ 3-Cl-2-pyridyl Cl H Me CF₃ 3-Cl-2-pyridylMe Cl Me CF₃ 3-Cl-2-pyridyl Cl Cl Me CF₃ 3-Cl-2-pyridyl Me Br Me CF₃3-Cl-2-pyridyl Cl Br Me CF₃ 3-Cl-2-pyridyl Me H Me Br 2-Cl-phenyl Cl HMe Br 2-Cl-phenyl Me Cl Me Br 2-Cl-phenyl Cl Cl Me Br 2-Cl-phenyl Me BrMe Br 2-Cl-phenyl Cl Br Me Br 2-Cl-phenyl Me H Me Br 3-Cl-2-pyridyl Cl HMe Br 3-Cl-2-pyridyl Me Cl Me Br 3-Cl-2-pyridyl Cl Cl Me Br3-Cl-2-pyridyl Me Br Me Br 3-Cl-2-pyridyl Cl Br Me Br 3-Cl-2-pyridyl MeH Me Cl 2-Cl-phenyl Cl H Me Cl 2-Cl-phenyl Me Cl Me Cl 2-Cl-phenyl Cl ClMe Cl 2-Cl-phenyl Me Br Me Cl 2-Cl-phenyl Cl Br Me Cl 2-Cl-phenyl Me HMe Cl 3-Cl-2-pyridyl Cl H Me Cl 3-Cl-2-pyridyl Me Cl Me Cl3-Cl-2-pyridyl Cl Cl Me Cl 3-Cl-2-pyridyl Me Br Me Cl 3-Cl-2-pyridyl ClBr Me Cl 3-Cl-2-pyridyl Me H i-Pr OCH₂CF₃ 2-Cl-phenyl Cl H i-Pr OCH₂CF₃2-Cl-phenyl Me Cl i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Cl i-Pr OCH₂CF₃2-Cl-phenyl Me Br i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Br i-Pr OCH₂CF₃2-Cl-phenyl Me H i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl H i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Cl i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Br i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Br i-Pr OCH₂CF₃3-Cl-2-pyridyl Me H i-Pr OCHF₂ 2-Cl-phenyl Cl H i-Pr OCHF₂ 2-Cl-phenylMe Cl i-Pr OCHF₂ 2-Cl-phenyl Cl Cl i-Pr OCHF₂ 2-Cl-phenyl Me Br i-PrOCHF₂ 2-Cl-phenyl Cl Br i-Pr OCHF₂ 2-Cl-phenyl Me H i-Pr OCHF₂3-Cl-2-pyridyl Cl H i-Pr OCHF₂ 3-Cl-2-pyridyl Me Cl i-Pr OCHF₂3-Cl-2-pyridyl Cl Cl i-Pr OCHF₂ 3-Cl-2-pyridyl Me Br i-Pr OCHF₂3-Cl-2-pyridyl Cl Br i-Pr OCHF₂ 3-Cl-2-pyridyl Me H i-Pr Me 2-Cl-phenylCl H i-Pr Me 2-Cl-phenyl Me Cl i-Pr Me 2-Cl-phenyl Cl Cl Me OCH₂CF₃2-Cl-phenyl Me Br Me OCH₂CF₃ 2-Cl-phenyl Cl Br Me OCH₂CF₃ 2-Cl-phenyl MeH Me OCH₂CF₃ 3-Cl-2-pyridyl Cl H Me OCH₂CF₃ 3-Cl-2-pyridyl Me Cl MeOCH₂CF₃ 3-Cl-2-pyridyl Cl Cl Me OCH₂CF₃ 3-Cl-2-pyridyl Me Br Me OCH₂CF₃3-Cl-2-pyridyl Cl Br Me OCH₂CF₃ 3-Cl-2-pyridyl Me H Me OCHF₂ 2-Cl-phenylCl H Me OCHF₂ 2-Cl-phenyl Me Cl Me OCHF₂ 2-Cl-phenyl Cl Cl Me OCHF₂2-Cl-phenyl Me Br Me OCHF₂ 2-Cl-phenyl Cl Br Me OCHF₂ 2-Cl-phenyl Me HMe OCHF₂ 3-Cl-2-pyridyl Cl H Me OCHF₂ 3-Cl-2-pyridyl Me Cl Me OCHF₂3-Cl-2-pyridyl Cl Cl Me OCHF₂ 3-Cl-2-pyridyl Me Br Me OCHF₂3-Cl-2-pyridyl Cl Br Me OCHF₂ 3-Cl-2-pyridyl

TABLE 9

R^(4a) R^(4b) R³ R^(5a) R^(5b) GR⁶ is OMe Me H i-Pr CF₃ 2-Cl-phenyl Cl Hi-Pr CF₃ 2-Cl-phenyl Me Cl i-Pr CF₃ 2-Cl-phenyl Cl Cl i-Pr CF₃2-Cl-phenyl Me Br i-Pr CF₃ 2-Cl-phenyl Cl Br i-Pr CF₃ 2-Cl-phenyl Me Hi-Pr CF₃ 3-Cl-2-pyridyl Cl H i-Pr CF₃ 3-Cl-2-pyridyl Me Cl i-Pr CF₃3-Cl-2-pyridyl Cl Cl i-Pr CF₃ 3-Cl-2-pyridyl Me Br i-Pr CF₃3-Cl-2-pyridyl Cl Br i-Pr CF₃ 3-Cl-2-pyridyl Me H i-Pr Br 2-Cl-phenyl ClH i-Pr Br 2-Cl-phenyl Me Cl i-Pr Br 2-Cl-phenyl Cl Cl i-Pr Br2-Cl-phenyl Me Br i-Pr Br 2-Cl-phenyl Cl Br i-Pr Br 2-Cl-phenyl Me Hi-Pr Br 3-Cl-2-pyridyl Cl H i-Pr Br 3-Cl-2-pyridyl Me Cl i-Pr Br3-Cl-2-pyridyl Cl Cl i-Pr Br 3-Cl-2-pyridyl Me Br i-Pr Br 3-Cl-2-pyridylCl Br i-Pr Br 3-Cl-2-pyridyl Me H i-Pr Cl 2-Cl-phenyl Cl H i-Pr Cl2-Cl-phenyl Me Cl i-Pr Cl 2-Cl-phenyl Cl Cl i-Pr Cl 2-Cl-phenyl Me Bri-Pr Cl 2-Cl-phenyl Cl Br i-Pr Cl 2-Cl-phenyl Me H i-Pr Cl3-Cl-2-pyridyl Cl H i-Pr Cl 3-Cl-2-pyridyl Me Cl i-Pr Cl 3-Cl-2-pyridylCl Cl i-Pr Cl 3-Cl-2-pyridyl Me Br i-Pr Cl 3-Cl-2-pyridyl Cl Br i-Pr Cl3-Cl-2-pyridyl Me H Me CF₃ 2-Cl-phenyl Cl H Me CF₃ 2-Cl-phenyl Me Cl MeCF₃ 2-Cl-phenyl Cl Cl Me CF₃ 2-Cl-phenyl Me Br Me CF₃ 2-Cl-phenyl Cl BrMe CF₃ 2-Cl-phenyl Me H Me CF₃ 3-Cl-2-pyridyl Cl H Me CF₃ 3-Cl-2-pyridylMe Cl Me CF₃ 3-Cl-2-pyridyl Cl Cl Me CF₃ 3-Cl-2-pyridyl Me Br Me CF₃3-Cl-2-pyridyl Cl Br Me CF₃ 3-Cl-2-pyridyl Me H Me Br 2-Cl-phenyl Cl HMe Br 2-Cl-phenyl Me Cl Me Br 2-Cl-phenyl Cl Cl Me Br 2-Cl-phenyl Me BrMe Br 2-Cl-phenyl Cl Br Me Br 2-Cl-phenyl Me H Me Br 3-Cl-2-pyridyl Cl HMe Br 3-Cl-2-pyridyl Me Cl Me Br 3-Cl-2-pyridyl Cl Cl Me Br3-Cl-2-pyridyl Me Br Me Br 3-Cl-2-pyridyl Cl Br Me Br 3-Cl-2-pyridyl MeH Me Cl 2-Cl-phenyl Cl H Me Cl 2-Cl-phenyl Me Cl Me Cl 2-Cl-phenyl Cl ClMe Cl 2-Cl-phenyl Me Br Me Cl 2-Cl-phenyl Cl Br Me Cl 2-Cl-phenyl Me HMe Cl 3-Cl-2-pyridyl Cl H Me Cl 3-Cl-2-pyridyl Me Cl Me Cl3-Cl-2-pyridyl Cl Cl Me Cl 3-Cl-2-pyridyl Me Br Me Cl 3-Cl-2-pyridyl ClBr Me Cl 3-Cl-2-pyridyl Me H i-Pr OCH₂CF₃ 2-Cl-phenyl Cl H i-Pr OCH₂CF₃2-Cl-phenyl Me Cl i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Cl i-Pr OCH₂CF₃2-Cl-phenyl Me Br i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Br i-Pr OCH₂CF₃2-Cl-phenyl Me H i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl H i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Cl i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Br i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Br i-Pr OCH₂CF₃3-Cl-2-pyridyl Me H i-Pr OCHF₂ 2-Cl-phenyl Cl H i-Pr OCHF₂ 2-Cl-phenylMe Cl i-Pr OCHF₂ 2-Cl-phenyl Cl Cl i-Pr OCHF₂ 2-Cl-phenyl Me Br i-PrOCHF₂ 2-Cl-phenyl Cl Br i-Pr OCHF₂ 2-Cl-phenyl Me H i-Pr OCHF₂3-Cl-2-pyridyl Cl H i-Pr OCHF₂ 3-Cl-2-pyridyl Me Cl i-Pr OCHF₂3-Cl-2-pyridyl Cl Cl i-Pr OCHF₂ 3-Cl-2-pyridyl Me Br i-Pr OCHF₂3-Cl-2-pyridyl Cl Br i-Pr OCHF₂ 3-Cl-2-pyridyl Me H Me OCH₂CF₃2-Cl-phenyl Cl H Me OCH₂CF₃ 2-Cl-phenyl Me Cl Me OCH₂CF₃ 2-Cl-phenyl ClCl Me OCH₂CF₃ 2-Cl-phenyl Me Br Me OCH₂CF₃ 2-Cl-phenyl Cl Br Me OCH₂CF₃2-Cl-phenyl Me H Me OCH₂CF₃ 3-Cl-2-pyridyl Cl H Me OCH₂CF₃3-Cl-2-pyridyl Me Cl Me OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl Me OCH₂CF₃3-Cl-2-pyridyl Me Br Me OCH₂CF₃ 3-Cl-2-pyridyl Cl Br Me OCH₂CF₃3-Cl-2-pyridyl Me H Me OCHF₂ 2-Cl-phenyl Cl H Me OCHF₂ 2-Cl-phenyl Me ClMe OCHF₂ 2-Cl-phenyl Cl Cl Me OCHF₂ 2-Cl-phenyl Me Br Me OCHF₂2-Cl-phenyl Cl Br Me OCHF₂ 2-Cl-phenyl Me H Me OCHF₂ 3-Cl-2-pyridyl Cl HMe OCHF₂ 3-Cl-2-pyridyl Me Cl Me OCHF₂ 3-Cl-2-pyridyl Cl Cl Me OCHF₂3-Cl-2-pyridyl Me Br Me OCHF₂ 3-Cl-2-pyridyl Cl Br Me OCHF₂3-Cl-2-pyridyl GR⁶ is SMe Me H i-Pr CF₃ 2-Cl-phenyl Cl H i-Pr CF₃2-Cl-phenyl Me Cl i-Pr CF₃ 2-Cl-phenyl Cl Cl i-Pr CF₃ 2-Cl-phenyl Me Bri-Pr CF₃ 2-Cl-phenyl Cl Br i-Pr CF₃ 2-Cl-phenyl Me H i-Pr CF₃3-Cl-2-pyridyl Cl H i-Pr CF₃ 3-Cl-2-pyridyl Me Cl i-Pr CF₃3-Cl-2-pyridyl Cl Cl i-Pr CF₃ 3-Cl-2-pyridyl Me Br i-Pr CF₃3-Cl-2-pyridyl Cl Br i-Pr CF₃ 3-Cl-2-pyridyl Me H i-Pr Br 2-Cl-phenyl ClH i-Pr Br 2-Cl-phenyl Me Cl i-Pr Br 2-Cl-phenyl Cl Cl i-Pr Br2-Cl-phenyl Me Br i-Pr Br 2-Cl-phenyl Cl Br i-Pr Br 2-Cl-phenyl Me Hi-Pr Br 3-Cl-2-pyridyl Cl H i-Pr Br 3-Cl-2-pyridyl Me Cl i-Pr Br3-Cl-2-pyridyl Cl Cl i-Pr Br 3-Cl-2-pyridyl Me Br i-Pr Br 3-Cl-2-pyridylCl Br i-Pr Br 3-Cl-2-pyridyl Me H i-Pr Cl 2-Cl-phenyl Cl H i-Pr Cl2-Cl-phenyl Me Cl i-Pr Cl 2-Cl-phenyl Cl Cl i-Pr Cl 2-Cl-phenyl Me Bri-Pr Cl 2-Cl-phenyl Cl Br i-Pr Cl 2-Cl-phenyl Me H i-Pr Cl3-Cl-2-pyridyl Cl H i-Pr Cl 3-Cl-2-pyridyl Me Cl i-Pr Cl 3-Cl-2-pyridylCl Cl i-Pr Cl 3-Cl-2-pyridyl Me Br i-Pr Cl 3-Cl-2-pyridyl Cl Br i-Pr Cl3-Cl-2-pyridyl Me H Me CF₃ 2-Cl-phenyl Cl H Me CF₃ 2-Cl-phenyl Me Cl MeCF₃ 2-Cl-phenyl Cl Cl Me CF₃ 2-Cl-phenyl Me Br Me CF₃ 2-Cl-phenyl Cl BrMe CF₃ 2-Cl-phenyl Me H Me CF₃ 3-Cl-2-pyridyl Cl H Me CF₃ 3-Cl-2-pyridylMe Cl Me CF₃ 3-Cl-2-pyridyl Cl Cl Me CF₃ 3-Cl-2-pyridyl Me Br Me CF₃3-Cl-2-pyridyl Cl Br Me CF₃ 3-Cl-2-pyridyl Me H Me Br 2-Cl-phenyl Cl HMe Br 2-Cl-phenyl Me Cl Me Br 2-Cl-phenyl Cl Cl Me Br 2-Cl-phenyl Me BrMe Br 2-Cl-phenyl Cl Br Me Br 2-Cl-phenyl Me H Me Br 3-Cl-2-pyridyl Cl HMe Br 3-Cl-2-pyridyl Me Cl Me Br 3-Cl-2-pyridyl Cl Cl Me Br3-Cl-2-pyridyl Me Br Me Br 3-Cl-2-pyridyl Cl Br Me Br 3-Cl-2-pyridyl MeH Me Cl 2-Cl-phenyl Cl H Me Cl 2-Cl-phenyl Me Cl Me Cl 2-Cl-phenyl Cl ClMe Cl 2-Cl-phenyl Me Br Me Cl 2-Cl-phenyl Cl Br Me Cl 2-Cl-phenyl Me HMe Cl 3-Cl-2-pyridyl Cl H Me Cl 3-Cl-2-pyridyl Me Cl Me Cl3-Cl-2-pyridyl Cl Cl Me Cl 3-Cl-2-pyridyl Me Br Me Cl 3-Cl-2-pyridyl ClBr Me Cl 3-Cl-2-pyridyl Me H i-Pr OCH₂CF₃ 2-Cl-phenyl Cl H i-Pr OCH₂CF₃2-Cl-phenyl Me Cl i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Cl i-Pr OCH₂CF₃2-Cl-phenyl Me Br i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Br i-Pr OCH₂CF₃2-Cl-phenyl Me H i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl H i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Cl i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Br i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Br i-Pr OCH₂CF₃3-Cl-2-pyridyl Me H i-Pr OCHF₂ 2-Cl-phenyl Cl H i-Pr OCHF₂ 2-Cl-phenylMe Cl i-Pr OCHF₂ 2-Cl-phenyl Cl Cl i-Pr OCHF₂ 2-Cl-phenyl Me Br i-PrOCHF₂ 2-Cl-phenyl Cl Br i-Pr OCHF₂ 2-Cl-phenyl Me H i-Pr OCHF₂3-Cl-2-pyridyl Cl H i-Pr OCHF₂ 3-Cl-2-pyridyl Me Cl i-Pr OCHF₂3-Cl-2-pyridyl Cl Cl i-Pr OCHF₂ 3-Cl-2-pyridyl Me Br i-Pr OCHF₂3-Cl-2-pyridyl Cl Br i-Pr OCHF₂ 3-Cl-2-pyridyl Me H i-Pr Me 2-Cl-phenylCl H i-Pr Me 2-Cl-phenyl Me Cl i-Pr Me 2-Cl-phenyl Cl Cl Me OCH₂CF₃2-Cl-phenyl Me Br Me OCH₂CF₃ 2-Cl-phenyl Cl Br Me OCH₂CF₃ 2-Cl-phenyl MeH Me OCH₂CF₃ 3-Cl-2-pyridyl Cl H Me OCH₂CF₃ 3-Cl-2-pyridyl Me Cl MeOCH₂CF₃ 3-Cl-2-pyridyl Cl Cl Me OCH₂CF₃ 3-Cl-2-pyridyl Me Br Me OCH₂CF₃3-Cl-2-pyridyl Cl Br Me OCH₂CF₃ 3-Cl-2-pyridyl Me H Me OCHF₂ 2-Cl-phenylCl H Me OCHF₂ 2-Cl-phenyl Me Cl Me OCHF₂ 2-Cl-phenyl Cl Cl Me OCHF₂2-Cl-phenyl Me Br Me OCHF₂ 2-Cl-phenyl Cl Br Me OCHF₂ 2-Cl-phenyl Me HMe OCHF₂ 3-Cl-2-pyridyl Cl H Me OCHF₂ 3-Cl-2-pyridyl Me Cl Me OCHF₂3-Cl-2-pyridyl Cl Cl Me OCHF₂ 3-Cl-2-pyridyl Me Br Me OCHF₂3-Cl-2-pyridyl Cl Br Me OCHF₂ 3-Cl-2-pyridyl GR⁶ is SCH₂Ph Me H i-Pr CF₃2-Cl-phenyl Cl H i-Pr CF₃ 2-Cl-phenyl Me Cl i-Pr CF₃ 2-Cl-phenyl Cl Cli-Pr CF₃ 2-Cl-phenyl Me Br i-Pr CF₃ 2-Cl-phenyl Cl Br i-Pr CF₃2-Cl-phenyl Me H i-Pr CF₃ 3-Cl-2-pyridyl Cl H i-Pr CF₃ 3-Cl-2-pyridyl MeCl i-Pr CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr CF₃ 3-Cl-2-pyridyl Me Br i-Pr CF₃3-Cl-2-pyridyl Cl Br i-Pr CF₃ 3-Cl-2-pyridyl Me H i-Pr Br 2-Cl-phenyl ClH i-Pr Br 2-Cl-phenyl Me Cl i-Pr Br 2-Cl-phenyl Cl Cl i-Pr Br2-Cl-phenyl Me Br i-Pr Br 2-Cl-phenyl Cl Br i-Pr Br 2-Cl-phenyl Me Hi-Pr Br 3-Cl-2-pyridyl Cl H i-Pr Br 3-Cl-2-pyridyl Me Cl i-Pr Br3-Cl-2-pyridyl Cl Cl i-Pr Br 3-Cl-2-pyridyl Me Br i-Pr Br 3-Cl-2-pyridylCl Br i-Pr Br 3-Cl-2-pyridyl Me H i-Pr Cl 2-Cl-phenyl Cl H i-Pr Cl2-Cl-phenyl Me Cl i-Pr Cl 2-Cl-phenyl Cl Cl i-Pr Cl 2-Cl-phenyl Me Bri-Pr Cl 2-Cl-phenyl Cl Br i-Pr Cl 2-Cl-phenyl Me H i-Pr Cl3-Cl-2-pyridyl Cl H i-Pr Cl 3-Cl-2-pyridyl Me Cl i-Pr Cl 3-Cl-2-pyridylCl Cl i-Pr Cl 3-Cl-2-pyridyl Me Br i-Pr Cl 3-Cl-2-pyridyl Cl Br i-Pr Cl3-Cl-2-pyridyl Me H Me CF₃ 2-Cl-phenyl Cl H Me CF₃ 2-Cl-phenyl Me Cl MeCF₃ 2-Cl-phenyl Cl Cl Me CF₃ 2-Cl-phenyl Me Br Me CF₃ 2-Cl-phenyl Cl BrMe CF₃ 2-Cl-phenyl Me H Me CF₃ 3-Cl-2-pyridyl Cl H Me CF₃ 3-Cl-2-pyridylMe Cl Me CF₃ 3-Cl-2-pyridyl Cl Cl Me CF₃ 3-Cl-2-pyridyl Me Br Me CF₃3-Cl-2-pyridyl Cl Br Me CF₃ 3-Cl-2-pyridyl Me H Me Br 2-Cl-phenyl Cl HMe Br 2-Cl-phenyl Me Cl Me Br 2-Cl-phenyl Cl Cl Me Br 2-Cl-phenyl Me BrMe Br 2-Cl-phenyl Cl Br Me Br 2-Cl-phenyl Me H Me Br 3-Cl-2-pyridyl Cl HMe Br 3-Cl-2-pyridyl Me Cl Me Br 3-Cl-2-pyridyl Cl Cl Me Br3-Cl-2-pyridyl Me Br Me Br 3-Cl-2-pyridyl Cl Br Me Br 3-Cl-2-pyridyl MeH Me Cl 2-Cl-phenyl Cl H Me Cl 2-Cl-phenyl Me Cl Me Cl 2-Cl-phenyl Cl ClMe Cl 2-Cl-phenyl Me Br Me Cl 2-Cl-phenyl Cl Br Me Cl 2-Cl-phenyl Me HMe Cl 3-Cl-2-pyridyl Cl H Me Cl 3-Cl-2-pyridyl Me Cl Me Cl3-Cl-2-pyridyl Cl Cl Me Cl 3-Cl-2-pyridyl Me Br Me Cl 3-Cl-2-pyridyl ClBr Me Cl 3-Cl-2-pyridyl Me H i-Pr OCH₂CF₃ 2-Cl-phenyl Cl H i-Pr OCH₂CF₃2-Cl-phenyl Me Cl i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Cl i-Pr OCH₂CF₃2-Cl-phenyl Me Br i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Br i-Pr OCH₂CF₃2-Cl-phenyl Me H i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl H i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Cl i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Br i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Br i-Pr OCH₂CF₃3-Cl-2-pyridyl Me H i-Pr OCHF₂ 2-Cl-phenyl Cl H i-Pr OCHF₂ 2-Cl-phenylMe Cl i-Pr OCHF₂ 2-Cl-phenyl Cl Cl i-Pr OCHF₂ 2-Cl-phenyl Me Br i-PrOCHF₂ 2-Cl-phenyl Cl Br i-Pr OCHF₂ 2-Cl-phenyl Me H i-Pr OCHF₂3-Cl-2-pyridyl Cl H i-Pr OCHF₂ 3-Cl-2-pyridyl Me Cl i-Pr OCHF₂3-Cl-2-pyridyl Cl Cl i-Pr OCHF₂ 3-Cl-2-pyridyl Me Br i-Pr OCHF₂3-Cl-2-pyridyl Cl Br i-Pr OCHF₂ 3-Cl-2-pyridyl Me H Me OCH₂CF₃2-Cl-phenyl Cl H Me OCH₂CF₃ 2-Cl-phenyl Me Cl Me OCH₂CF₃ 2-Cl-phenyl ClCl Me OCH₂CF₃ 2-Cl-phenyl Me Br Me OCH₂CF₃ 2-Cl-phenyl Cl Br Me OCH₂CF₃2-Cl-phenyl Me H Me OCH₂CF₃ 3-Cl-2-pyridyl Cl H Me OCH₂CF₃3-Cl-2-pyridyl Me Cl Me OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl Me OCH₂CF₃3-Cl-2-pyridyl Me Br Me OCH₂CF₃ 3-Cl-2-pyridyl Cl Br Me OCH₂CF₃3-Cl-2-pyridyl Me H Me OCHF₂ 2-Cl-phenyl Cl H Me OCHF₂ 2-Cl-phenyl Me ClMe OCHF₂ 2-Cl-phenyl Cl Cl Me OCHF₂ 2-Cl-phenyl Me Br Me OCHF₂2-Cl-phenyl Cl Br Me OCHF₂ 2-Cl-phenyl Me H Me OCHF₂ 3-Cl-2-pyridyl Cl HMe OCHF₂ 3-Cl-2-pyridyl Me Cl Me OCHF₂ 3-Cl-2-pyridyl Cl Cl Me OCHF₂3-Cl-2-pyridyl Me Br Me OCHF₂ 3-Cl-2-pyridyl Cl Br Me OCHF₂3-Cl-2-pyridyl GR⁶ is NMe₂ Me H i-Pr CF₃ 2-Cl-phenyl Cl H i-Pr CF₃2-Cl-phenyl Me Cl i-Pr CF₃ 2-Cl-phenyl Cl Cl i-Pr CF₃ 2-Cl-phenyl Me Bri-Pr CF₃ 2-Cl-phenyl Cl Br i-Pr CF₃ 2-Cl-phenyl Me H i-Pr CF₃3-Cl-2-pyridyl Cl H i-Pr CF₃ 3-Cl-2-pyridyl Me Cl i-Pr CF₃3-Cl-2-pyridyl Cl Cl i-Pr CF₃ 3-Cl-2-pyridyl Me Br i-Pr CF₃3-Cl-2-pyridyl Cl Br i-Pr CF₃ 3-Cl-2-pyridyl Me H i-Pr Br 2-Cl-phenyl ClH i-Pr Br 2-Cl-phenyl Me Cl i-Pr Br 2-Cl-phenyl Cl Cl i-Pr Br2-Cl-phenyl Me Br i-Pr Br 2-Cl-phenyl Cl Br i-Pr Br 2-Cl-phenyl Me Hi-Pr Br 3-Cl-2-pyridyl Cl H i-Pr Br 3-Cl-2-pyridyl Me Cl i-Pr Br3-Cl-2-pyridyl Cl Cl i-Pr Br 3-Cl-2-pyridyl Me Br i-Pr Br 3-Cl-2-pyridylCl Br i-Pr Br 3-Cl-2-pyridyl Me H i-Pr Cl 2-Cl-phenyl Cl H i-Pr Cl2-Cl-phenyl Me Cl i-Pr Cl 2-Cl-phenyl Cl Cl i-Pr Cl 2-Cl-phenyl Me Bri-Pr Cl 2-Cl-phenyl Cl Br i-Pr Cl 2-Cl-phenyl Me H i-Pr Cl3-Cl-2-pyridyl Cl H i-Pr Cl 3-Cl-2-pyridyl Me Cl i-Pr Cl 3-Cl-2-pyridylCl Cl i-Pr Cl 3-Cl-2-pyridyl Me Br i-Pr Cl 3-Cl-2-pyridyl Cl Br i-Pr Cl3-Cl-2-pyridyl Me H Me CF₃ 2-Cl-phenyl Cl H Me CF₃ 2-Cl-phenyl Me Cl MeCF₃ 2-Cl-phenyl Cl Cl Me CF₃ 2-Cl-phenyl Me Br Me CF₃ 2-Cl-phenyl Cl BrMe CF₃ 2-Cl-phenyl Me H Me CF₃ 3-Cl-2-pyridyl Cl H Me CF₃ 3-Cl-2-pyridylMe Cl Me CF₃ 3-Cl-2-pyridyl Cl Cl Me CF₃ 3-Cl-2-pyridyl Me Br Me CF₃3-Cl-2-pyridyl Cl Br Me CF₃ 3-Cl-2-pyridyl Me H Me Br 2-Cl-phenyl Cl HMe Br 2-Cl-phenyl Me Cl Me Br 2-Cl-phenyl Cl Cl Me Br 2-Cl-phenyl Me BrMe Br 2-Cl-phenyl Cl Br Me Br 2-Cl-phenyl Me H Me Br 3-Cl-2-pyridyl Cl HMe Br 3-Cl-2-pyridyl Me Cl Me Br 3-Cl-2-pyridyl Cl Cl Me Br3-Cl-2-pyridyl Me Br Me Br 3-Cl-2-pyridyl Cl Br Me Br 3-Cl-2-pyridyl MeH Me Cl 2-Cl-phenyl Cl H Me Cl 2-Cl-phenyl Me Cl Me Cl 2-Cl-phenyl Cl ClMe Cl 2-Cl-phenyl Me Br Me Cl 2-Cl-phenyl Cl Br Me Cl 2-Cl-phenyl Me HMe Cl 3-Cl-2-pyridyl Cl H Me Cl 3-Cl-2-pyridyl Me Cl Me Cl3-Cl-2-pyridyl Cl Cl Me Cl 3-Cl-2-pyridyl Me Br Me Cl 3-Cl-2-pyridyl ClBr Me Cl 3-Cl-2-pyridyl Me H i-Pr OCH₂CF₃ 2-Cl-phenyl Cl H i-Pr OCH₂CF₃2-Cl-phenyl Me Cl i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Cl i-Pr OCH₂CF₃2-Cl-phenyl Me Br i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Br i-Pr OCH₂CF₃2-Cl-phenyl Me H i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl H i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Cl i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Br i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Br i-Pr OCH₂CF₃3-Cl-2-pyridyl Me H i-Pr OCHF₂ 2-Cl-phenyl Cl H i-Pr OCHF₂ 2-Cl-phenylMe Cl i-Pr OCHF₂ 2-Cl-phenyl Cl Cl i-Pr OCHF₂ 2-Cl-phenyl Me Br i-PrOCHF₂ 2-Cl-phenyl Cl Br i-Pr OCHF₂ 2-Cl-phenyl Me H i-Pr OCHF₂3-Cl-2-pyridyl Cl H i-Pr OCHF₂ 3-Cl-2-pyridyl Me Cl i-Pr OCHF₂3-Cl-2-pyridyl Cl Cl i-Pr OCHF₂ 3-Cl-2-pyridyl Me Br i-Pr OCHF₂3-Cl-2-pyridyl Cl Br i-Pr OCHF₂ 3-Cl-2-pyridyl Me H i-Pr Me 2-Cl-phenylCl H i-Pr Me 2-Cl-phenyl Me Cl i-Pr Me 2-Cl-phenyl Cl Cl Me OCH₂CF₃2-Cl-phenyl Me Br Me OCH₂CF₃ 2-Cl-phenyl Cl Br Me OCH₂CF₃ 2-Cl-phenyl MeH Me OCH₂CF₃ 3-Cl-2-pyridyl Cl H Me OCH₂CF₃ 3-Cl-2-pyridyl Me Cl MeOCH₂CF₃ 3-Cl-2-pyridyl Cl Cl Me OCH₂CF₃ 3-Cl-2-pyridyl Me Br Me OCH₂CF₃3-Cl-2-pyridyl Cl Br Me OCH₂CF₃ 3-Cl-2-pyridyl Me H Me OCHF₂ 2-Cl-phenylCl H Me OCHF₂ 2-Cl-phenyl Me Cl Me OCHF₂ 2-Cl-phenyl Cl Cl Me OCHF₂2-Cl-phenyl Me Br Me OCHF₂ 2-Cl-phenyl Cl Br Me OCHF₂ 2-Cl-phenyl Me HMe OCHF₂ 3-Cl-2-pyridyl Cl H Me OCHF₂ 3-Cl-2-pyridyl Me Cl Me OCHF₂3-Cl-2-pyridyl Cl Cl Me OCHF₂ 3-Cl-2-pyridyl Me Br Me OCHF₂3-Cl-2-pyridyl Cl Br Me OCHF₂ 3-Cl-2-pyridyl

TABLE 10

R^(4a) R^(4b) R³ R^(5a) R^(5b) Me H i-Pr CF₃ 2-Cl-phenyl Cl H i-Pr CF₃2-Cl-phenyl Me Cl i-Pr CF₃ 2-Cl-phenyl Cl Cl i-Pr CF₃ 2-Cl-phenyl Me Bri-Pr CF₃ 2-Cl-phenyl Cl Br i-Pr CF₃ 2-Cl-phenyl Me H i-Pr CF₃3-Cl-2-pyridyl Cl H i-Pr CF₃ 3-Cl-2-pyridyl Me Cl i-Pr CF₃3-Cl-2-pyridyl Cl Cl i-Pr CF₃ 3-Cl-2-pyridyl Me Br i-Pr CF₃3-Cl-2-pyridyl Cl Br i-Pr CF₃ 3-Cl-2-pyridyl Me H i-Pr Br 2-Cl-phenyl ClH i-Pr Br 2-Cl-phenyl Me Cl i-Pr Br 2-Cl-phenyl Cl Cl i-Pr Br2-Cl-phenyl Me Br i-Pr Br 2-Cl-phenyl Cl Br i-Pr Br 2-Cl-phenyl Me Hi-Pr Br 3-Cl-2-pyridyl Cl H i-Pr Br 3-Cl-2-pyridyl Me Cl i-Pr Br3-Cl-2-pyridyl Cl Cl i-Pr Br 3-Cl-2-pyridyl Me Br i-Pr Br 3-Cl-2-pyridylCl Br i-Pr Br 3-Cl-2-pyridyl Me H i-Pr Cl 2-Cl-phenyl Cl H i-Pr Cl2-Cl-phenyl Me Cl i-Pr Cl 2-Cl-phenyl Cl Cl i-Pr Cl 2-Cl-phenyl Me Bri-Pr Cl 2-Cl-phenyl Cl Br i-Pr Cl 2-Cl-phenyl Me H i-Pr Cl3-Cl-2-pyridyl Cl H i-Pr Cl 3-Cl-2-pyridyl Me Cl i-Pr Cl 3-Cl-2-pyridylCl Cl i-Pr Cl 3-Cl-2-pyridyl Me Br i-Pr Cl 3-Cl-2-pyridyl Cl Br i-Pr Cl3-Cl-2-pyridyl Me H Me CF₃ 2-Cl-phenyl Cl H Me CF₃ 2-Cl-phenyl Me Cl MeCF₃ 2-Cl-phenyl Cl Cl Me CF₃ 2-Cl-phenyl Me Br Me CF₃ 2-Cl-phenyl Cl BrMe CF₃ 2-Cl-phenyl Me H Me CF₃ 3-Cl-2-pyridyl Cl H Me CF₃ 3-Cl-2-pyridylMe Cl Me CF₃ 3-Cl-2-pyridyl Cl Cl Me CF₃ 3-Cl-2-pyridyl Me Br Me CF₃3-Cl-2-pyridyl Cl Br Me CF₃ 3-Cl-2-pyridyl Me H Me Br 2-Cl-phenyl Cl HMe Br 2-Cl-phenyl Me Cl Me Br 2-Cl-phenyl Cl Cl Me Br 2-Cl-phenyl Me BrMe Br 2-Cl-phenyl Cl Br Me Br 2-Cl-phenyl Me H Me Br 3-Cl-2-pyridyl Cl HMe Br 3-Cl-2-pyridyl Me Cl Me Br 3-Cl-2-pyridyl Cl Cl Me Br3-Cl-2-pyridyl Me Br Me Br 3-Cl-2-pyridyl Cl Br Me Br 3-Cl-2-pyridyl MeH Me Cl 2-Cl-phenyl Cl H Me Cl 2-Cl-phenyl Me Cl Me Cl 2-Cl-phenyl Cl ClMe Cl 2-Cl-phenyl Me Br Me Cl 2-Cl-phenyl Cl Br Me Cl 2-Cl-phenyl Me HMe Cl 3-Cl-2-pyridyl Cl H Me Cl 3-Cl-2-pyridyl Me Cl Me Cl3-Cl-2-pyridyl Cl Cl Me Cl 3-Cl-2-pyridyl Me Br Me Cl 3-Cl-2-pyridyl ClBr Me Cl 3-Cl-2-pyridyl Me H i-Pr OCH₂CF₃ 2-Cl-phenyl Cl H i-Pr OCH₂CF₃2-Cl-phenyl Me Cl i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Cl i-Pr OCH₂CF₃2-Cl-phenyl Me Br i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Br i-Pr OCH₂CF₃2-Cl-phenyl Me H i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl H i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Cl i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Br i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Br i-Pr OCH₂CF₃3-Cl-2-pyridyl Me H i-Pr OCHF₂ 2-Cl-phenyl Cl H i-Pr OCHF₂ 2-Cl-phenylMe Cl i-Pr OCHF₂ 2-Cl-phenyl Cl Cl i-Pr OCHF₂ 2-Cl-phenyl Me Br i-PrOCHF₂ 2-Cl-phenyl Cl Br i-Pr OCHF₂ 2-Cl-phenyl Me H i-Pr OCHF₂3-Cl-2-pyridyl Cl H i-Pr OCHF₂ 3-Cl-2-pyridyl Me Cl i-Pr OCHF₂3-Cl-2-pyridyl Cl Cl i-Pr OCHF₂ 3-Cl-2-pyridyl Me Br i-Pr OCHF₂3-Cl-2-pyridyl Cl Br i-Pr OCHF₂ 3-Cl-2-pyridyl Me H Me OCH₂CF₃2-Cl-phenyl Cl H Me OCH₂CF₃ 2-Cl-phenyl Me Cl Me OCH₂CF₃ 2-Cl-phenyl ClCl Me OCH₂CF₃ 2-Cl-phenyl Me Br Me OCH₂CF₃ 2-Cl-phenyl Cl Br Me OCH₂CF₃2-Cl-phenyl Me H Me OCH₂CF₃ 3-Cl-2-pyridyl Cl H Me OCH₂CF₃3-Cl-2-pyridyl Me Cl Me OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl Me OCH₂CF₃3-Cl-2-pyridyl Me Br Me OCH₂CF₃ 3-Cl-2-pyridyl Cl Br Me OCH₂CF₃3-Cl-2-pyridyl Me H Me OCHF₂ 2-Cl-phenyl Cl H Me OCHF₂ 2-Cl-phenyl Me ClMe OCHF₂ 2-Cl-phenyl Cl Cl Me OCHF₂ 2-Cl-phenyl Me Br Me OCHF₂2-Cl-phenyl Cl Br Me OCHF₂ 2-Cl-phenyl Me H Me OCHF₂ 3-Cl-2-pyridyl Cl HMe OCHF₂ 3-Cl-2-pyridyl Me Cl Me OCHF₂ 3-Cl-2-pyridyl Cl Cl Me OCHF₂3-Cl-2-pyridyl Me Br Me OCHF₂ 3-Cl-2-pyridyl Cl Br Me OCHF₂3-Cl-2-pyridyl Me H i-Pr CF₃ 2-Cl-phenyl Cl H i-Pr CF₃ 2-Cl-phenyl Me Cli-Pr CF₃ 2-Cl-phenyl Cl Cl i-Pr CF₃ 2-Cl-phenyl Me Br i-Pr CF₃2-Cl-phenyl Cl Br i-Pr CF₃ 2-Cl-phenyl Me H i-Pr CF₃ 3-Cl-2-pyridyl Cl Hi-Pr CF₃ 3-Cl-2-pyridyl Me Cl i-Pr CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr CF₃3-Cl-2-pyridyl Me Br i-Pr CF₃ 3-Cl-2-pyridyl Cl Br i-Pr CF₃3-Cl-2-pyridyl Me H i-Pr Br 2-Cl-phenyl Cl H i-Pr Br 2-Cl-phenyl Me Cli-Pr Br 2-Cl-phenyl Cl Cl i-Pr Br 2-Cl-phenyl Me Br i-Pr Br 2-Cl-phenylCl Br i-Pr Br 2-Cl-phenyl Me H i-Pr Br 3-Cl-2-pyridyl Cl H i-Pr Br3-Cl-2-pyridyl Me Cl i-Pr Br 3-Cl-2-pyridyl Cl Cl i-Pr Br 3-Cl-2-pyridylMe Br i-Pr Br 3-Cl-2-pyridyl Cl Br i-Pr Br 3-Cl-2-pyridyl Me H i-Pr Cl2-Cl-phenyl Cl H i-Pr Cl 2-Cl-phenyl Me Cl i-Pr Cl 2-Cl-phenyl Cl Cli-Pr Cl 2-Cl-phenyl Me Br i-Pr Cl 2-Cl-phenyl Cl Br i-Pr Cl 2-Cl-phenylMe H i-Pr Cl 3-Cl-2-pyridyl Cl H i-Pr Cl 3-Cl-2-pyridyl Me Cl i-Pr Cl3-Cl-2-pyridyl Cl Cl i-Pr Cl 3-Cl-2-pyridyl Me Br i-Pr Cl 3-Cl-2-pyridylCl Br i-Pr Cl 3-Cl-2-pyridyl Me H Me CF₃ 2-Cl-phenyl Cl H Me CF₃2-Cl-phenyl Me Cl Me CF₃ 2-Cl-phenyl Cl Cl Me CF₃ 2-Cl-phenyl Me Br MeCF₃ 2-Cl-phenyl Cl Br Me CF₃ 2-Cl-phenyl Me H Me CF₃ 3-Cl-2-pyridyl Cl HMe CF₃ 3-Cl-2-pyridyl Me Cl Me CF₃ 3-Cl-2-pyridyl Cl Cl Me CF₃3-Cl-2-pyridyl Me Br Me CF₃ 3-Cl-2-pyridyl Cl Br Me CF₃ 3-Cl-2-pyridylMe H Me Br 2-Cl-phenyl Cl H Me Br 2-Cl-phenyl Me Cl Me Br 2-Cl-phenyl ClCl Me Br 2-Cl-phenyl Me Br Me Br 2-Cl-phenyl Cl Br Me Br 2-Cl-phenyl MeH Me Br 3-Cl-2-pyridyl Cl H Me Br 3-Cl-2-pyridyl Me Cl Me Br3-Cl-2-pyridyl Cl Cl Me Br 3-Cl-2-pyridyl Me Br Me Br 3-Cl-2-pyridyl ClBr Me Br 3-Cl-2-pyridyl Me H Me Cl 2-Cl-phenyl Cl H Me Cl 2-Cl-phenyl MeCl Me Cl 2-Cl-phenyl Cl Cl Me Cl 2-Cl-phenyl Me Br Me Cl 2-Cl-phenyl ClBr Me Cl 2-Cl-phenyl Me H Me Cl 3-Cl-2-pyridyl Cl H Me Cl 3-Cl-2-pyridylMe Cl Me Cl 3-Cl-2-pyridyl Cl Cl Me Cl 3-Cl-2-pyridyl Me Br Me Cl3-Cl-2-pyridyl Cl Br Me Cl 3-Cl-2-pyridyl Me H i-Pr OCH₂CF₃ 2-Cl-phenylCl H i-Pr OCH₂CF₃ 2-Cl-phenyl Me Cl i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Cl i-PrOCH₂CF₃ 2-Cl-phenyl Me Br i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Br i-Pr OCH₂CF₃2-Cl-phenyl Me H i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl H i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Cl i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Br i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Br i-Pr OCH₂CF₃3-Cl-2-pyridyl Me H i-Pr OCHF₂ 2-Cl-phenyl Cl H i-Pr OCHF₂ 2-Cl-phenylMe Cl i-Pr OCHF₂ 2-Cl-phenyl Cl Cl i-Pr OCHF₂ 2-Cl-phenyl Me Br i-PrOCHF₂ 2-Cl-phenyl Cl Br i-Pr OCHF₂ 2-Cl-phenyl Me H i-Pr OCHF₂3-Cl-2-pyridyl Cl H i-Pr OCHF₂ 3-Cl-2-pyridyl Me Cl i-Pr OCHF₂3-Cl-2-pyridyl Cl Cl i-Pr OCHF₂ 3-Cl-2-pyridyl Me Br i-Pr OCHF₂3-Cl-2-pyridyl Cl Br i-Pr OCHF₂ 3-Cl-2-pyridyl Me H i-Pr Me 2-Cl-phenylCl H i-Pr Me 2-Cl-phenyl Me Cl i-Pr Me 2-Cl-phenyl Cl Cl Me OCH₂CF₃2-Cl-phenyl Me Br Me OCH₂CF₃ 2-Cl-phenyl Cl Br Me OCH₂CF₃ 2-Cl-phenyl MeH Me OCH₂CF₃ 3-Cl-2-pyridyl Cl H Me OCH₂CF₃ 3-Cl-2-pyridyl Me Cl MeOCH₂CF₃ 3-Cl-2-pyridyl Cl Cl Me OCH₂CF₃ 3-Cl-2-pyridyl Me Br Me OCH₂CF₃3-Cl-2-pyridyl Cl Br Me OCH₂CF₃ 3-Cl-2-pyridyl Me H Me OCHF₂ 2-Cl-phenylCl H Me OCHF₂ 2-Cl-phenyl Me Cl Me OCHF₂ 2-Cl-phenyl Cl Cl Me OCHF₂2-Cl-phenyl Me Br Me OCHF₂ 2-Cl-phenyl Cl Br Me OCHF₂ 2-Cl-phenyl Me HMe OCHF₂ 3-Cl-2-pyridyl Cl H Me OCHF₂ 3-Cl-2-pyridyl Me Cl Me OCHF₂3-Cl-2-pyridyl Cl Cl Me OCHF₂ 3-Cl-2-pyridyl Me Br Me OCHF₂3-Cl-2-pyridyl Cl Br Me OCHF₂ 3-Cl-2-pyridyl

TABLE 11

R^(4a) R^(4b) R³ R^(5a) R^(5b) Me H i-Pr CF₃ 2-Cl-phenyl Cl H i-Pr CF₃2-Cl-phenyl Me Cl i-Pr CF₃ 2-Cl-phenyl Cl Cl i-Pr CF₃ 2-Cl-phenyl Me Bri-Pr CF₃ 2-Cl-phenyl Cl Br i-Pr CF₃ 2-Cl-phenyl Me H i-Pr CF₃3-Cl-2-pyridyl Cl H i-Pr CF₃ 3-Cl-2-pyridyl Me Cl i-Pr CF₃3-Cl-2-pyridyl Cl Cl i-Pr CF₃ 3-Cl-2-pyridyl Me Br i-Pr CF₃3-Cl-2-pyridyl Cl Br i-Pr CF₃ 3-Cl-2-pyridyl Me H i-Pr Br 2-Cl-phenyl ClH i-Pr Br 2-Cl-phenyl Me Cl i-Pr Br 2-Cl-phenyl Cl Cl i-Pr Br2-Cl-phenyl Me Br i-Pr Br 2-Cl-phenyl Cl Br i-Pr Br 2-Cl-phenyl Me Hi-Pr Br 3-Cl-2-pyridyl Cl H i-Pr Br 3-Cl-2-pyridyl Me Cl i-Pr Br3-Cl-2-pyridyl Cl Cl i-Pr Br 3-Cl-2-pyridyl Me Br i-Pr Br 3-Cl-2-pyridylCl Br i-Pr Br 3-Cl-2-pyridyl Me H i-Pr Cl 2-Cl-phenyl Cl H i-Pr Cl2-Cl-phenyl Me Cl i-Pr Cl 2-Cl-phenyl Cl Cl i-Pr Cl 2-Cl-phenyl Me Bri-Pr Cl 2-Cl-phenyl Cl Br i-Pr Cl 2-Cl-phenyl Me H i-Pr Cl3-Cl-2-pyridyl Cl H i-Pr Cl 3-Cl-2-pyridyl Me Cl i-Pr Cl 3-Cl-2-pyridylCl Cl i-Pr Cl 3-Cl-2-pyridyl Me Br i-Pr Cl 3-Cl-2-pyridyl Cl Br i-Pr Cl3-Cl-2-pyridyl Me H Me CF₃ 2-Cl-phenyl Cl H Me CF₃ 2-Cl-phenyl Me Cl MeCF₃ 2-Cl-phenyl Cl Cl Me CF₃ 2-Cl-phenyl Me Br Me CF₃ 2-Cl-phenyl Cl BrMe CF₃ 2-Cl-phenyl Me H Me CF₃ 3-Cl-2-pyridyl Cl H Me CF₃ 3-Cl-2-pyridylMe Cl Me CF₃ 3-Cl-2-pyridyl Cl Cl Me CF₃ 3-Cl-2-pyridyl Me Br Me CF₃3-Cl-2-pyridyl Cl Br Me CF₃ 3-Cl-2-pyridyl Me H Me Br 2-Cl-phenyl Cl HMe Br 2-Cl-phenyl Me Cl Me Br 2-Cl-phenyl Cl Cl Me Br 2-Cl-phenyl Me BrMe Br 2-Cl-phenyl Cl Br Me Br 2-Cl-phenyl Me H Me Br 3-Cl-2-pyridyl Cl HMe Br 3-Cl-2-pyridyl Me Cl Me Br 3-Cl-2-pyridyl Cl Cl Me Br3-Cl-2-pyridyl Me Br Me Br 3-Cl-2-pyridyl Cl Br Me Br 3-Cl-2-pyridyl MeH Me Cl 2-Cl-phenyl Cl H Me Cl 2-Cl-phenyl Me Cl Me Cl 2-Cl-phenyl Cl ClMe Cl 2-Cl-phenyl Me Br Me Cl 2-Cl-phenyl Cl Br Me Cl 2-Cl-phenyl Me HMe Cl 3-Cl-2-pyridyl Cl H Me Cl 3-Cl-2-pyridyl Me Cl Me Cl3-Cl-2-pyridyl Cl Cl Me Cl 3-Cl-2-pyridyl Me Br Me Cl 3-Cl-2-pyridyl ClBr Me Cl 3-Cl-2-pyridyl Me H i-Pr OCH₂CF₃ 2-Cl-phenyl Cl H i-Pr OCH₂CF₃2-Cl-phenyl Me Cl i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Cl i-Pr OCH₂CF₃2-Cl-phenyl Me Br i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Br i-Pr OCH₂CF₃2-Cl-phenyl Me H i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl H i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Cl i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Br i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Br i-Pr OCH₂CF₃3-Cl-2-pyridyl Me H i-Pr OCHF₂ 2-Cl-phenyl Cl H i-Pr OCHF₂ 2-Cl-phenylMe Cl i-Pr OCHF₂ 2-Cl-phenyl Cl Cl i-Pr OCHF₂ 2-Cl-phenyl Me Br i-PrOCHF₂ 2-Cl-phenyl Cl Br i-Pr OCHF₂ 2-Cl-phenyl Me H i-Pr OCHF₂3-Cl-2-pyridyl Cl H i-Pr OCHF₂ 3-Cl-2-pyridyl Me Cl i-Pr OCHF₂3-Cl-2-pyridyl Cl Cl i-Pr OCHF₂ 3-Cl-2-pyridyl Me Br i-Pr OCHF₂3-Cl-2-pyridyl Cl Br i-Pr OCHF₂ 3-Cl-2-pyridyl Me H Me OCH₂CF₃2-Cl-phenyl Cl H Me OCH₂CF₃ 2-Cl-phenyl Me Cl Me OCH₂CF₃ 2-Cl-phenyl ClCl Me OCH₂CF₃ 2-Cl-phenyl Me Br Me OCH₂CF₃ 2-Cl-phenyl Cl Br Me OCH₂CF₃2-Cl-phenyl Me H Me OCH₂CF₃ 3-Cl-2-pyridyl Cl H Me OCH₂CF₃3-Cl-2-pyridyl Me Cl Me OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl Me OCH₂CF₃3-Cl-2-pyridyl Me Br Me OCH₂CF₃ 3-Cl-2-pyridyl Cl Br Me OCH₂CF₃3-Cl-2-pyridyl Me H Me OCHF₂ 2-Cl-phenyl Cl H Me OCHF₂ 2-Cl-phenyl Me ClMe OCHF₂ 2-Cl-phenyl Cl Cl Me OCHF₂ 2-Cl-phenyl Me Br Me OCHF₂2-Cl-phenyl Cl Br Me OCHF₂ 2-Cl-phenyl Me H Me OCHF₂ 3-Cl-2-pyridyl Cl HMe OCHF₂ 3-Cl-2-pyridyl Me Cl Me OCHF₂ 3-Cl-2-pyridyl Cl Cl Me OCHF₂3-Cl-2-pyridyl Me Br Me OCHF₂ 3-Cl-2-pyridyl Cl Br Me OCHF₂3-Cl-2-pyridyl Me H i-Pr CF₃ 2-Cl-phenyl Cl H i-Pr CF₃ 2-Cl-phenyl Me Cli-Pr CF₃ 2-Cl-phenyl Cl Cl i-Pr CF₃ 2-Cl-phenyl Me Br i-Pr CF₃2-Cl-phenyl Cl Br i-Pr CF₃ 2-Cl-phenyl Me H i-Pr CF₃ 3-Cl-2-pyridyl Cl Hi-Pr CF₃ 3-Cl-2-pyridyl Me Cl i-Pr CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr CF₃3-Cl-2-pyridyl Me Br i-Pr CF₃ 3-Cl-2-pyridyl Cl Br i-Pr CF₃3-Cl-2-pyridyl Me H i-Pr Br 2-Cl-phenyl Cl H i-Pr Br 2-Cl-phenyl Me Cli-Pr Br 2-Cl-phenyl Cl Cl i-Pr Br 2-Cl-phenyl Me Br i-Pr Br 2-Cl-phenylCl Br i-Pr Br 2-Cl-phenyl Me H i-Pr Br 3-Cl-2-pyridyl Cl H i-Pr Br3-Cl-2-pyridyl Me Cl i-Pr Br 3-Cl-2-pyridyl Cl Cl i-Pr Br 3-Cl-2-pyridylMe Br i-Pr Br 3-Cl-2-pyridyl Cl Br i-Pr Br 3-Cl-2-pyridyl Me H i-Pr Cl2-Cl-phenyl Cl H i-Pr Cl 2-Cl-phenyl Me Cl i-Pr Cl 2-Cl-phenyl Cl Cli-Pr Cl 2-Cl-phenyl Me Br i-Pr Cl 2-Cl-phenyl Cl Br i-Pr Cl 2-Cl-phenylMe H i-Pr Cl 3-Cl-2-pyridyl Cl H i-Pr Cl 3-Cl-2-pyridyl Me Cl i-Pr Cl3-Cl-2-pyridyl Cl Cl i-Pr Cl 3-Cl-2-pyridyl Me Br i-Pr Cl 3-Cl-2-pyridylCl Br i-Pr Cl 3-Cl-2-pyridyl Me H Me CF₃ 2-Cl-phenyl Cl H Me CF₃2-Cl-phenyl Me Cl Me CF₃ 2-Cl-phenyl Cl Cl Me CF₃ 2-Cl-phenyl Me Br MeCF₃ 2-Cl-phenyl Cl Br Me CF₃ 2-Cl-phenyl Me H Me CF₃ 3-Cl-2-pyridyl Cl HMe CF₃ 3-Cl-2-pyridyl Me Cl Me CF₃ 3-Cl-2-pyridyl Cl Cl Me CF₃3-Cl-2-pyridyl Me Br Me CF₃ 3-Cl-2-pyridyl Cl Br Me CF₃ 3-Cl-2-pyridylMe H Me Br 2-Cl-phenyl Cl H Me Br 2-Cl-phenyl Me Cl Me Br 2-Cl-phenyl ClCl Me Br 2-Cl-phenyl Me Br Me Br 2-Cl-phenyl Cl Br Me Br 2-Cl-phenyl MeH Me Br 3-Cl-2-pyridyl Cl H Me Br 3-Cl-2-pyridyl Me Cl Me Br3-Cl-2-pyridyl Cl Cl Me Br 3-Cl-2-pyridyl Me Br Me Br 3-Cl-2-pyridyl ClBr Me Br 3-Cl-2-pyridyl Me H Me Cl 2-Cl-phenyl Cl H Me Cl 2-Cl-phenyl MeCl Me Cl 2-Cl-phenyl Cl Cl Me Cl 2-Cl-phenyl Me Br Me Cl 2-Cl-phenyl ClBr Me Cl 2-Cl-phenyl Me H Me Cl 3-Cl-2-pyridyl Cl H Me Cl 3-Cl-2-pyridylMe Cl Me Cl 3-Cl-2-pyridyl Cl Cl Me Cl 3-Cl-2-pyridyl Me Br Me Cl3-Cl-2-pyridyl Cl Br Me Cl 3-Cl-2-pyridyl Me H i-Pr OCH₂CF₃ 2-Cl-phenylCl H i-Pr OCH₂CF₃ 2-Cl-phenyl Me Cl i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Cl i-PrOCH₂CF₃ 2-Cl-phenyl Me Br i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Br i-Pr OCH₂CF₃2-Cl-phenyl Me H i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl H i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Cl i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Br i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Br i-Pr OCH₂CF₃3-Cl-2-pyridyl Me H i-Pr OCHF₂ 2-Cl-phenyl Cl H i-Pr OCHF₂ 2-Cl-phenylMe Cl i-Pr OCHF₂ 2-Cl-phenyl Cl Cl i-Pr OCHF₂ 2-Cl-phenyl Me Br i-PrOCHF₂ 2-Cl-phenyl Cl Br i-Pr OCHF₂ 2-Cl-phenyl Me H i-Pr OCHF₂3-Cl-2-pyridyl Cl H i-Pr OCHF₂ 3-Cl-2-pyridyl Me Cl i-Pr OCHF₂3-Cl-2-pyridyl Cl Cl i-Pr OCHF₂ 3-Cl-2-pyridyl Me Br i-Pr OCHF₂3-Cl-2-pyridyl Cl Br i-Pr OCHF₂ 3-Cl-2-pyridyl Me H i-Pr Me 2-Cl-phenylCl H i-Pr Me 2-Cl-phenyl Me Cl i-Pr Me 2-Cl-phenyl Cl Cl Me OCH₂CF₃2-Cl-phenyl Me Br Me OCH₂CF₃ 2-Cl-phenyl Cl Br Me OCH₂CF₃ 2-Cl-phenyl MeH Me OCH₂CF₃ 3-Cl-2-pyridyl Cl H Me OCH₂CF₃ 3-Cl-2-pyridyl Me Cl MeOCH₂CF₃ 3-Cl-2-pyridyl Cl Cl Me OCH₂CF₃ 3-Cl-2-pyridyl Me Br Me OCH₂CF₃3-Cl-2-pyridyl Cl Br Me OCH₂CF₃ 3-Cl-2-pyridyl Me H Me OCHF₂ 2-Cl-phenylCl H Me OCHF₂ 2-Cl-phenyl Me Cl Me OCHF₂ 2-Cl-phenyl Cl Cl Me OCHF₂2-Cl-phenyl Me Br Me OCHF₂ 2-Cl-phenyl Cl Br Me OCHF₂ 2-Cl-phenyl Me HMe OCHF₂ 3-Cl-2-pyridyl Cl H Me OCHF₂ 3-Cl-2-pyridyl Me Cl Me OCHF₂3-Cl-2-pyridyl Cl Cl Me OCHF₂ 3-Cl-2-pyridyl Me Br Me OCHF₂3-Cl-2-pyridyl Cl Br Me OCHF₂ 3-Cl-2-pyridyl

TABLE 12

R^(4a) R^(4b) R³ R^(5a) R^(5b) Me H i-Pr CF₃ 2-Cl-phenyl Cl H i-Pr CF₃2-Cl-phenyl Me Cl i-Pr CF₃ 2-Cl-phenyl Cl Cl i-Pr CF₃ 2-Cl-phenyl Me Bri-Pr CF₃ 2-Cl-phenyl Cl Br i-Pr CF₃ 2-Cl-phenyl Me H i-Pr CF₃3-Cl-2-pyridyl Cl H i-Pr CF₃ 3-Cl-2-pyridyl Me Cl i-Pr CF₃3-Cl-2-pyridyl Cl Cl i-Pr CF₃ 3-Cl-2-pyridyl Me Br i-Pr CF₃3-Cl-2-pyridyl Cl Br i-Pr CF₃ 3-Cl-2-pyridyl Me H i-Pr Br 2-Cl-phenyl ClH i-Pr Br 2-Cl-phenyl Me Cl i-Pr Br 2-Cl-phenyl Cl Cl i-Pr Br2-Cl-phenyl Me Br i-Pr Br 2-Cl-phenyl Cl Br i-Pr Br 2-Cl-phenyl Me Hi-Pr Br 3-Cl-2-pyridyl Cl H i-Pr Br 3-Cl-2-pyridyl Me Cl i-Pr Br3-Cl-2-pyridyl Cl Cl i-Pr Br 3-Cl-2-pyridyl Me Br i-Pr Br 3-Cl-2-pyridylCl Br i-Pr Br 3-Cl-2-pyridyl Me H i-Pr Cl 2-Cl-phenyl Cl H i-Pr Cl2-Cl-phenyl Me Cl i-Pr Cl 2-Cl-phenyl Cl Cl i-Pr Cl 2-Cl-phenyl Me Bri-Pr Cl 2-Cl-phenyl Cl Br i-Pr Cl 2-Cl-phenyl Me H i-Pr Cl3-Cl-2-pyridyl Cl H i-Pr Cl 3-Cl-2-pyridyl Me Cl i-Pr Cl 3-Cl-2-pyridylCl Cl i-Pr Cl 3-Cl-2-pyridyl Me Br i-Pr Cl 3-Cl-2-pyridyl Cl Br i-Pr Cl3-Cl-2-pyridyl Me H Me CF₃ 2-Cl-phenyl Cl H Me CF₃ 2-Cl-phenyl Me Cl MeCF₃ 2-Cl-phenyl Cl Cl Me CF₃ 2-Cl-phenyl Me Br Me CF₃ 2-Cl-phenyl Cl BrMe CF₃ 2-Cl-phenyl Me H Me CF₃ 3-Cl-2-pyridyl Cl H Me CF₃ 3-Cl-2-pyridylMe Cl Me CF₃ 3-Cl-2-pyridyl Cl Cl Me CF₃ 3-Cl-2-pyridyl Me Br Me CF₃3-Cl-2-pyridyl Cl Br Me CF₃ 3-Cl-2-pyridyl Me H Me Br 2-Cl-phenyl Cl HMe Br 2-Cl-phenyl Me Cl Me Br 2-Cl-phenyl Cl Cl Me Br 2-Cl-phenyl Me BrMe Br 2-Cl-phenyl Cl Br Me Br 2-Cl-phenyl Me H Me Br 3-Cl-2-pyridyl Cl HMe Br 3-Cl-2-pyridyl Me Cl Me Br 3-Cl-2-pyridyl Cl Cl Me Br3-Cl-2-pyridyl Me Br Me Br 3-Cl-2-pyridyl Cl Br Me Br 3-Cl-2-pyridyl MeH Me Cl 2-Cl-phenyl Cl H Me Cl 2-Cl-phenyl Me Cl Me Cl 2-Cl-phenyl Cl ClMe Cl 2-Cl-phenyl Me Br Me Cl 2-Cl-phenyl Cl Br Me Cl 2-Cl-phenyl Me HMe Cl 3-Cl-2-pyridyl Cl H Me Cl 3-Cl-2-pyridyl Me Cl Me Cl3-Cl-2-pyridyl Cl Cl Me Cl 3-Cl-2-pyridyl Me Br Me Cl 3-Cl-2-pyridyl ClBr Me Cl 3-Cl-2-pyridyl Me H i-Pr OCH₂CF₃ 2-Cl-phenyl Cl H i-Pr OCH₂CF₃2-Cl-phenyl Me Cl i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Cl i-Pr OCH₂CF₃2-Cl-phenyl Me Br i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Br i-Pr OCH₂CF₃2-Cl-phenyl Me H i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl H i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Cl i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Br i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Br i-Pr OCH₂CF₃3-Cl-2-pyridyl Me H i-Pr OCHF₂ 2-Cl-phenyl Cl H i-Pr OCHF₂ 2-Cl-phenylMe Cl i-Pr OCHF₂ 2-Cl-phenyl Cl Cl i-Pr OCHF₂ 2-Cl-phenyl Me Br i-PrOCHF₂ 2-Cl-phenyl Cl Br i-Pr OCHF₂ 2-Cl-phenyl Me H i-Pr OCHF₂3-Cl-2-pyridyl Cl H i-Pr OCHF₂ 3-Cl-2-pyridyl Me Cl i-Pr OCHF₂3-Cl-2-pyridyl Cl Cl i-Pr OCHF₂ 3-Cl-2-pyridyl Me Br i-Pr OCHF₂3-Cl-2-pyridyl Cl Br i-Pr OCHF₂ 3-Cl-2-pyridyl Me H Me OCH₂CF₃2-Cl-phenyl Cl H Me OCH₂CF₃ 2-Cl-phenyl Me Cl Me OCH₂CF₃ 2-Cl-phenyl ClCl Me OCH₂CF₃ 2-Cl-phenyl Me Br Me OCH₂CF₃ 2-Cl-phenyl Cl Br Me OCH₂CF₃2-Cl-phenyl Me H Me OCH₂CF₃ 3-Cl-2-pyridyl Cl H Me OCH₂CF₃3-Cl-2-pyridyl Me Cl Me OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl Me OCH₂CF₃3-Cl-2-pyridyl Me Br Me OCH₂CF₃ 3-Cl-2-pyridyl Cl Br Me OCH₂CF₃3-Cl-2-pyridyl Me H Me OCHF₂ 2-Cl-phenyl Cl H Me OCHF₂ 2-Cl-phenyl Me ClMe OCHF₂ 2-Cl-phenyl Cl Cl Me OCHF₂ 2-Cl-phenyl Me Br Me OCHF₂2-Cl-phenyl Cl Br Me OCHF₂ 2-Cl-phenyl Me H Me OCHF₂ 3-Cl-2-pyridyl Cl HMe OCHF₂ 3-Cl-2-pyridyl Me Cl Me OCHF₂ 3-Cl-2-pyridyl Cl Cl Me OCHF₂3-Cl-2-pyridyl Me Br Me OCHF₂ 3-Cl-2-pyridyl Cl Br Me OCHF₂3-Cl-2-pyridyl Me H i-Pr CF₃ 2-Cl-phenyl Cl H i-Pr CF₃ 2-Cl-phenyl Me Cli-Pr CF₃ 2-Cl-phenyl Cl Cl i-Pr CF₃ 2-Cl-phenyl Me Br i-Pr CF₃2-Cl-phenyl Cl Br i-Pr CF₃ 2-Cl-phenyl Me H i-Pr CF₃ 3-Cl-2-pyridyl Cl Hi-Pr CF₃ 3-Cl-2-pyridyl Me Cl i-Pr CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr CF₃3-Cl-2-pyridyl Me Br i-Pr CF₃ 3-Cl-2-pyridyl Cl Br i-Pr CF₃3-Cl-2-pyridyl Me H i-Pr Br 2-Cl-phenyl Cl H i-Pr Br 2-Cl-phenyl Me Cli-Pr Br 2-Cl-phenyl Cl Cl i-Pr Br 2-Cl-phenyl Me Br i-Pr Br 2-Cl-phenylCl Br i-Pr Br 2-Cl-phenyl Me H i-Pr Br 3-Cl-2-pyridyl Cl H i-Pr Br3-Cl-2-pyridyl Me Cl i-Pr Br 3-Cl-2-pyridyl Cl Cl i-Pr Br 3-Cl-2-pyridylMe Br i-Pr Br 3-Cl-2-pyridyl Cl Br i-Pr Br 3-Cl-2-pyridyl Me H i-Pr Cl2-Cl-phenyl Cl H i-Pr Cl 2-Cl-phenyl Me Cl i-Pr Cl 2-Cl-phenyl Cl Cli-Pr Cl 2-Cl-phenyl Me Br i-Pr Cl 2-Cl-phenyl Cl Br i-Pr Cl 2-Cl-phenylMe H i-Pr Cl 3-Cl-2-pyridyl Cl H i-Pr Cl 3-Cl-2-pyridyl Me Cl i-Pr Cl3-Cl-2-pyridyl Cl Cl i-Pr Cl 3-Cl-2-pyridyl Me Br i-Pr Cl 3-Cl-2-pyridylCl Br i-Pr Cl 3-Cl-2-pyridyl Me H Me CF₃ 2-Cl-phenyl Cl H Me CF₃2-Cl-phenyl Me Cl Me CF₃ 2-Cl-phenyl Cl Cl Me CF₃ 2-Cl-phenyl Me Br MeCF₃ 2-Cl-phenyl Cl Br Me CF₃ 2-Cl-phenyl Me H Me CF₃ 3-Cl-2-pyridyl Cl HMe CF₃ 3-Cl-2-pyridyl Me Cl Me CF₃ 3-Cl-2-pyridyl Cl Cl Me CF₃3-Cl-2-pyridyl Me Br Me CF₃ 3-Cl-2-pyridyl Cl Br Me CF₃ 3-Cl-2-pyridylMe H Me Br 2-Cl-phenyl Cl H Me Br 2-Cl-phenyl Me Cl Me Br 2-Cl-phenyl ClCl Me Br 2-Cl-phenyl Me Br Me Br 2-Cl-phenyl Cl Br Me Br 2-Cl-phenyl MeH Me Br 3-Cl-2-pyridyl Cl H Me Br 3-Cl-2-pyridyl Me Cl Me Br3-Cl-2-pyridyl Cl Cl Me Br 3-Cl-2-pyridyl Me Br Me Br 3-Cl-2-pyridyl ClBr Me Br 3-Cl-2-pyridyl Me H Me Cl 2-Cl-phenyl Cl H Me Cl 2-Cl-phenyl MeCl Me Cl 2-Cl-phenyl Cl Cl Me Cl 2-Cl-phenyl Me Br Me Cl 2-Cl-phenyl ClBr Me Cl 2-Cl-phenyl Me H Me Cl 3-Cl-2-pyridyl Cl H Me Cl 3-Cl-2-pyridylMe Cl Me Cl 3-Cl-2-pyridyl Cl Cl Me Cl 3-Cl-2-pyridyl Me Br Me Cl3-Cl-2-pyridyl Cl Br Me Cl 3-Cl-2-pyridyl Me H i-Pr OCH₂CF₃ 2-Cl-phenylCl H i-Pr OCH₂CF₃ 2-Cl-phenyl Me Cl i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Cl i-PrOCH₂CF₃ 2-Cl-phenyl Me Br i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Br i-Pr OCH₂CF₃2-Cl-phenyl Me H i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl H i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Cl i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Br i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Br i-Pr OCH₂CF₃3-Cl-2-pyridyl Me H i-Pr OCHF₂ 2-Cl-phenyl Cl H i-Pr OCHF₂ 2-Cl-phenylMe Cl i-Pr OCHF₂ 2-Cl-phenyl Cl Cl i-Pr OCHF₂ 2-Cl-phenyl Me Br i-PrOCHF₂ 2-Cl-phenyl Cl Br i-Pr OCHF₂ 2-Cl-phenyl Me H i-Pr OCHF₂3-Cl-2-pyridyl Cl H i-Pr OCHF₂ 3-Cl-2-pyridyl Me Cl i-Pr OCHF₂3-Cl-2-pyridyl Cl Cl i-Pr OCHF₂ 3-Cl-2-pyridyl Me Br i-Pr OCHF₂3-Cl-2-pyridyl Cl Br i-Pr OCHF₂ 3-Cl-2-pyridyl Me H i-Pr Me 2-Cl-phenylCl H i-Pr Me 2-Cl-phenyl Me Cl i-Pr Me 2-Cl-phenyl Cl Cl Me OCH₂CF₃2-Cl-phenyl Me Br Me OCH₂CF₃ 2-Cl-phenyl Cl Br Me OCH₂CF₃ 2-Cl-phenyl MeH Me OCH₂CF₃ 3-Cl-2-pyridyl Cl H Me OCH₂CF₃ 3-Cl-2-pyridyl Me Cl MeOCH₂CF₃ 3-Cl-2-pyridyl Cl Cl Me OCH₂CF₃ 3-Cl-2-pyridyl Me Br Me OCH₂CF₃3-Cl-2-pyridyl Cl Br Me OCH₂CF₃ 3-Cl-2-pyridyl Me H Me OCHF₂ 2-Cl-phenylCl H Me OCHF₂ 2-Cl-phenyl Me Cl Me OCHF₂ 2-Cl-phenyl Cl Cl Me OCHF₂2-Cl-phenyl Me Br Me OCHF₂ 2-Cl-phenyl Cl Br Me OCHF₂ 2-Cl-phenyl Me HMe OCHF₂ 3-Cl-2-pyridyl Cl H Me OCHF₂ 3-Cl-2-pyridyl Me Cl Me OCHF₂3-Cl-2-pyridyl Cl Cl Me OCHF₂ 3-Cl-2-pyridyl Me Br Me OCHF₂3-Cl-2-pyridyl Cl Br Me OCHF₂ 3-Cl-2-pyridyl

TABLE 13

R^(4a) R^(4b) R³ R^(5a) R^(5b) Me H i-Pr CF₃ 2-Cl-phenyl Cl H i-Pr CF₃2-Cl-phenyl Me Cl i-Pr CF₃ 2-Cl-phenyl Cl Cl i-Pr CF₃ 2-Cl-phenyl Me Bri-Pr CF₃ 2-Cl-phenyl Cl Br i-Pr CF₃ 2-Cl-phenyl Me H i-Pr CF₃3-Cl-2-pyridyl Cl H i-Pr CF₃ 3-Cl-2-pyridyl Me Cl i-Pr CF₃3-Cl-2-pyridyl Cl Cl i-Pr CF₃ 3-Cl-2-pyridyl Me Br i-Pr CF₃3-Cl-2-pyridyl Cl Br i-Pr CF₃ 3-Cl-2-pyridyl Me H i-Pr Br 2-Cl-phenyl ClH i-Pr Br 2-Cl-phenyl Me Cl i-Pr Br 2-Cl-phenyl Cl Cl i-Pr Br2-Cl-phenyl Me Br i-Pr Br 2-Cl-phenyl Cl Br i-Pr Br 2-Cl-phenyl Me Hi-Pr Br 3-Cl-2-pyridyl Cl H i-Pr Br 3-Cl-2-pyridyl Me Cl i-Pr Br3-Cl-2-pyridyl Cl Cl i-Pr Br 3-Cl-2-pyridyl Me Br i-Pr Br 3-Cl-2-pyridylCl Br i-Pr Br 3-Cl-2-pyridyl Me H i-Pr Cl 2-Cl-phenyl Cl H i-Pr Cl2-Cl-phenyl Me Cl i-Pr Cl 2-Cl-phenyl Cl Cl i-Pr Cl 2-Cl-phenyl Me Bri-Pr Cl 2-Cl-phenyl Cl Br i-Pr Cl 2-Cl-phenyl Me H i-Pr Cl3-Cl-2-pyridyl Cl H i-Pr Cl 3-Cl-2-pyridyl Me Cl i-Pr Cl 3-Cl-2-pyridylCl Cl i-Pr Cl 3-Cl-2-pyridyl Me Br i-Pr Cl 3-Cl-2-pyridyl Cl Br i-Pr Cl3-Cl-2-pyridyl Me H Me CF₃ 2-Cl-phenyl Cl H Me CF₃ 2-Cl-phenyl Me Cl MeCF₃ 2-Cl-phenyl Cl Cl Me CF₃ 2-Cl-phenyl Me Br Me CF₃ 2-Cl-phenyl Cl BrMe CF₃ 2-Cl-phenyl Me H Me CF₃ 3-Cl-2-pyridyl Cl H Me CF₃ 3-Cl-2-pyridylMe Cl Me CF₃ 3-Cl-2-pyridyl Cl Cl Me CF₃ 3-Cl-2-pyridyl Me Br Me CF₃3-Cl-2-pyridyl Cl Br Me CF₃ 3-Cl-2-pyridyl Me H Me Br 2-Cl-phenyl Cl HMe Br 2-Cl-phenyl Me Cl Me Br 2-Cl-phenyl Cl Cl Me Br 2-Cl-phenyl Me BrMe Br 2-Cl-phenyl Cl Br Me Br 2-Cl-phenyl Me H Me Br 3-Cl-2-pyridyl Cl HMe Br 3-Cl-2-pyridyl Me Cl Me Br 3-Cl-2-pyridyl Cl Cl Me Br3-Cl-2-pyridyl Me Br Me Br 3-Cl-2-pyridyl Cl Br Me Br 3-Cl-2-pyridyl MeH Me Cl 2-Cl-phenyl Cl H Me Cl 2-Cl-phenyl Me Cl Me Cl 2-Cl-phenyl Cl ClMe Cl 2-Cl-phenyl Me Br Me Cl 2-Cl-phenyl Cl Br Me Cl 2-Cl-phenyl Me HMe Cl 3-Cl-2-pyridyl Cl H Me Cl 3-Cl-2-pyridyl Me Cl Me Cl3-Cl-2-pyridyl Cl Cl Me Cl 3-Cl-2-pyridyl Me Br Me Cl 3-Cl-2-pyridyl ClBr Me Cl 3-Cl-2-pyridyl Me H i-Pr OCH₂CF₃ 2-Cl-phenyl Cl H i-Pr OCH₂CF₃2-Cl-phenyl Me Cl i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Cl i-Pr OCH₂CF₃2-Cl-phenyl Me Br i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Br i-Pr OCH₂CF₃2-Cl-phenyl Me H i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl H i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Cl i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Br i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Br i-Pr OCH₂CF₃3-Cl-2-pyridyl Me H i-Pr OCHF₂ 2-Cl-phenyl Cl H i-Pr OCHF₂ 2-Cl-phenylMe Cl i-Pr OCHF₂ 2-Cl-phenyl Cl Cl i-Pr OCHF₂ 2-Cl-phenyl Me Br i-PrOCHF₂ 2-Cl-phenyl Cl Br i-Pr OCHF₂ 2-Cl-phenyl Me H i-Pr OCHF₂3-Cl-2-pyridyl Cl H i-Pr OCHF₂ 3-Cl-2-pyridyl Me Cl i-Pr OCHF₂3-Cl-2-pyridyl Cl Cl i-Pr OCHF₂ 3-Cl-2-pyridyl Me Br i-Pr OCHF₂3-Cl-2-pyridyl Cl Br i-Pr OCHF₂ 3-Cl-2-pyridyl Me H Me OCH₂CF₃2-Cl-phenyl Cl H Me OCH₂CF₃ 2-Cl-phenyl Me Cl Me OCH₂CF₃ 2-Cl-phenyl ClCl Me OCH₂CF₃ 2-Cl-phenyl Me Br Me OCH₂CF₃ 2-Cl-phenyl Cl Br Me OCH₂CF₃2-Cl-phenyl Me H Me OCH₂CF₃ 3-Cl-2-pyridyl Cl H Me OCH₂CF₃3-Cl-2-pyridyl Me Cl Me OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl Me OCH₂CF₃3-Cl-2-pyridyl Me Br Me OCH₂CF₃ 3-Cl-2-pyridyl Cl Br Me OCH₂CF₃3-Cl-2-pyridyl Me H Me OCHF₂ 2-Cl-phenyl Cl H Me OCHF₂ 2-Cl-phenyl Me ClMe OCHF₂ 2-Cl-phenyl Cl Cl Me OCHF₂ 2-Cl-phenyl Me Br Me OCHF₂2-Cl-phenyl Cl Br Me OCHF₂ 2-Cl-phenyl Me H Me OCHF₂ 3-Cl-2-pyridyl Cl HMe OCHF₂ 3-Cl-2-pyridyl Me Cl Me OCHF₂ 3-Cl-2-pyridyl Cl Cl Me OCHF₂3-Cl-2-pyridyl Me Br Me OCHF₂ 3-Cl-2-pyridyl Cl Br Me OCHF₂3-Cl-2-pyridyl Me H i-Pr CF₃ 2-Cl-phenyl Cl H i-Pr CF₃ 2-Cl-phenyl Me Cli-Pr CF₃ 2-Cl-phenyl Cl Cl i-Pr CF₃ 2-Cl-phenyl Me Br i-Pr CF₃2-Cl-phenyl Cl Br i-Pr CF₃ 2-Cl-phenyl Me H i-Pr CF₃ 3-Cl-2-pyridyl Cl Hi-Pr CF₃ 3-Cl-2-pyridyl Me Cl i-Pr CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr CF₃3-Cl-2-pyridyl Me Br i-Pr CF₃ 3-Cl-2-pyridyl Cl Br i-Pr CF₃3-Cl-2-pyridyl Me H i-Pr Br 2-Cl-phenyl Cl H i-Pr Br 2-Cl-phenyl Me Cli-Pr Br 2-Cl-phenyl Cl Cl i-Pr Br 2-Cl-phenyl Me Br i-Pr Br 2-Cl-phenylCl Br i-Pr Br 2-Cl-phenyl Me H i-Pr Br 3-Cl-2-pyridyl Cl H i-Pr Br3-Cl-2-pyridyl Me Cl i-Pr Br 3-Cl-2-pyridyl Cl Cl i-Pr Br 3-Cl-2-pyridylMe Br i-Pr Br 3-Cl-2-pyridyl Cl Br i-Pr Br 3-Cl-2-pyridyl Me H i-Pr Cl2-Cl-phenyl Cl H i-Pr Cl 2-Cl-phenyl Me Cl i-Pr Cl 2-Cl-phenyl Cl Cli-Pr Cl 2-Cl-phenyl Me Br i-Pr Cl 2-Cl-phenyl Cl Br i-Pr Cl 2-Cl-phenylMe H i-Pr Cl 3-Cl-2-pyridyl Cl H i-Pr Cl 3-Cl-2-pyridyl Me Cl i-Pr Cl3-Cl-2-pyridyl Cl Cl i-Pr Cl 3-Cl-2-pyridyl Me Br i-Pr Cl 3-Cl-2-pyridylCl Br i-Pr Cl 3-Cl-2-pyridyl Me H Me CF₃ 2-Cl-phenyl Cl H Me CF₃2-Cl-phenyl Me Cl Me CF₃ 2-Cl-phenyl Cl Cl Me CF₃ 2-Cl-phenyl Me Br MeCF₃ 2-Cl-phenyl Cl Br Me CF₃ 2-Cl-phenyl Me H Me CF₃ 3-Cl-2-pyridyl Cl HMe CF₃ 3-Cl-2-pyridyl Me Cl Me CF₃ 3-Cl-2-pyridyl Cl Cl Me CF₃3-Cl-2-pyridyl Me Br Me CF₃ 3-Cl-2-pyridyl Cl Br Me CF₃ 3-Cl-2-pyridylMe H Me Br 2-Cl-phenyl Cl H Me Br 2-Cl-phenyl Me Cl Me Br 2-Cl-phenyl ClCl Me Br 2-Cl-phenyl Me Br Me Br 2-Cl-phenyl Cl Br Me Br 2-Cl-phenyl MeH Me Br 3-Cl-2-pyridyl Cl H Me Br 3-Cl-2-pyridyl Me Cl Me Br3-Cl-2-pyridyl Cl Cl Me Br 3-Cl-2-pyridyl Me Br Me Br 3-Cl-2-pyridyl ClBr Me Br 3-Cl-2-pyridyl Me H Me Cl 2-Cl-phenyl Cl H Me Cl 2-Cl-phenyl MeCl Me Cl 2-Cl-phenyl Cl Cl Me Cl 2-Cl-phenyl Me Br Me Cl 2-Cl-phenyl ClBr Me Cl 2-Cl-phenyl Me H Me Cl 3-Cl-2-pyridyl Cl H Me Cl 3-Cl-2-pyridylMe Cl Me Cl 3-Cl-2-pyridyl Cl Cl Me Cl 3-Cl-2-pyridyl Me Br Me Cl3-Cl-2-pyridyl Cl Br Me Cl 3-Cl-2-pyridyl Me H i-Pr OCH₂CF₃ 2-Cl-phenylCl H i-Pr OCH₂CF₃ 2-Cl-phenyl Me Cl i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Cl i-PrOCH₂CF₃ 2-Cl-phenyl Me Br i-Pr OCH₂CF₃ 2-Cl-phenyl Cl Br i-Pr OCH₂CF₃2-Cl-phenyl Me H i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl H i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Cl i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Cl i-Pr OCH₂CF₃3-Cl-2-pyridyl Me Br i-Pr OCH₂CF₃ 3-Cl-2-pyridyl Cl Br i-Pr OCH₂CF₃3-Cl-2-pyridyl Me H i-Pr OCHF₂ 2-Cl-phenyl Cl H i-Pr OCHF₂ 2-Cl-phenylMe Cl i-Pr OCHF₂ 2-Cl-phenyl Cl Cl i-Pr OCHF₂ 2-Cl-phenyl Me Br i-PrOCHF₂ 2-Cl-phenyl Cl Br i-Pr OCHF₂ 2-Cl-phenyl Me H i-Pr OCHF₂3-Cl-2-pyridyl Cl H i-Pr OCHF₂ 3-Cl-2-pyridyl Me Cl i-Pr OCHF₂3-Cl-2-pyridyl Cl Cl i-Pr OCHF₂ 3-Cl-2-pyridyl Me Br i-Pr OCHF₂3-Cl-2-pyridyl Cl Br i-Pr OCHF₂ 3-Cl-2-pyridyl Me H i-Pr Me 2-Cl-phenylCl H i-Pr Me 2-Cl-phenyl Me Cl i-Pr Me 2-Cl-phenyl Cl Cl Me OCH₂CF₃2-Cl-phenyl Me Br Me OCH₂CF₃ 2-Cl-phenyl Cl Br Me OCH₂CF₃ 2-Cl-phenyl MeH Me OCH₂CF₃ 3-Cl-2-pyridyl Cl H Me OCH₂CF₃ 3-Cl-2-pyridyl Me Cl MeOCH₂CF₃ 3-Cl-2-pyridyl Cl Cl Me OCH₂CF₃ 3-Cl-2-pyridyl Me Br Me OCH₂CF₃3-Cl-2-pyridyl Cl Br Me OCH₂CF₃ 3-Cl-2-pyridyl Me H Me OCHF₂ 2-Cl-phenylCl H Me OCHF₂ 2-Cl-phenyl Me Cl Me OCHF₂ 2-Cl-phenyl Cl Cl Me OCHF₂2-Cl-phenyl Me Br Me OCHF₂ 2-Cl-phenyl Cl Br Me OCHF₂ 2-Cl-phenyl Me HMe OCHF₂ 3-Cl-2-pyridyl Cl H Me OCHF₂ 3-Cl-2-pyridyl Me Cl Me OCHF₂3-Cl-2-pyridyl Cl Cl Me OCHF₂ 3-Cl-2-pyridyl Me Br Me OCHF₂3-Cl-2-pyridyl Cl Br Me OCHF₂ 3-Cl-2-pyridylFormulation/Utility

Compounds of this invention will generally be used as a formulation orcomposition with an agriculturally suitable carrier comprising at leastone of a liquid diluent, a solid diluent or a surfactant. Theformulation or composition ingredients are selected to be consistentwith the physical properties of the active ingredient, mode ofapplication and environmental factors such as soil type, moisture andtemperature. Useful formulations include liquids such as solutions(including emulsifiable concentrates), suspensions, emulsions (includingmicroemulsions and/or suspoemulsions) and the like which optionally canbe thickened into gels. Useful formulations further include solids suchas dusts, powders, granules, pellets, tablets, films, and the like whichcan be water-dispersible (“wettable”) or water-soluble. Activeingredient can be (micro)encapsulated and further formed into asuspension or solid formulation; alternatively the entire formulation ofactive ingredient can be encapsulated (or “overcoated”). Encapsulationcan control or delay release of the active ingredient. Sprayableformulations can be extended in suitable media and used at spray volumesfrom about one to several hundred liters per hectare. High-strengthcompositions are primarily used as intermediates for furtherformulation.

The formulations will typically contain effective amounts of activeingredient, diluent and surfactant within the following approximateranges that add up to 100 percent by weight.

Weight Percent Active Ingredient Diluent Surfactant Water-Dispersibleand Water-soluble 5-90 0-94 1-15 Granules, Tablets and Powders.Suspensions, Emulsions, Solutions 5-50 40-95  0-15 (includingEmulsifiable Concentrates) Dusts 1-25 70-99  0-5  Granules and Pellets0.01-99     5-99.99 0-15 High Strength Compositions 90-99  0-10 0-2 

Typical solid diluents are described in Watkins, et al., Handbook ofInsecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books,Caldwell, N.J. Typical liquid diluents are described in Marsden,Solvents Guide, 2nd Ed., Interscience, N.Y., 1950. McCutcheon'sDetergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, N.J.,as well as Sisely and Wood, Encyclopedia of Surface Active Agents,Chemical Publ. Co., Inc., New York, 1964, list surfactants andrecommended uses. All formulations can contain minor amounts ofadditives to reduce foam, caking, corrosion, microbiological growth andthe like, or thickeners to increase viscosity.

Surfactants include, for example, polyethoxylated alcohols,polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acidesters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzenesulfonates, organosilicones, N,N-dialkyltaurates, lignin sulfonates,naphthalene sulfonate formaldehyde condensates, polycarboxylates, andpolyoxyethylene/polyoxypropylene block copolymers. Solid diluentsinclude, for example, clays such as bentonite, montmorillonite,attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth,urea, calcium carbonate, sodium carbonate and bicarbonate, and sodiumsulfate. Liquid diluents include, for example, water,N,N-dimethylformamide, dimethyl sulfoxide, N-alkylpyrrolidone, ethyleneglycol, polypropylene glycol, paraffins, alkylbenzenes,alkylnaphthalenes, oils of olive, castor, linseed, tung, sesame, corn,peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters,ketones such as cyclohexalnone, 2-heptanone, isophorone and4-hydroxy-4-methyl-2-pentanone, and alcohols such as methanol,cyclohexanol, decanol and tetrahydrofurfuryl alcohol.

Solutions, including emulsifiable concentrates, can be prepared bysimply mixing the ingredients. Dusts and powders can be prepared byblending and, usually, grinding as in a hammer mill or fluid-energymill. Suspensions are usually prepared by wet-milling; see, for example,U.S. Pat. No. 3,060,084. Granules and pellets can be prepared byspraying the active material upon preformed granular carriers or byagglomeration techniques. See Browning, “Agglomeration”, ChemicalEngineering, Dec. 4, 1967, pp 147-48, Perry's Chemical Engineer'sHandbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 andfollowing, and PCT Publication WO 91/13546. Pellets can be prepared asdescribed in U.S. Pat. No. 4,172,714. Water-dispersible andwater-soluble granules can be prepared as taught in U.S. Pat. No.4,144,050, U.S. Pat. No. 3,920,442 and DE 3,246,493. Tablets can beprepared as taught in U.S. Pat. No. 5,180,587, U.S. Pat. No. 5,232,701and U.S. Pat. No. 5,208,030. Films can be prepared as taught in GB2,095,558 and U.S. Pat. No. 3,299,566.

For further information regarding the art of formulation, see T. S.Woods, “The Formulator's Toolbox—Product Forms for Modern Agriculture”in Pesticide Chemistry and Bioscience, The Food-Environment Challenge,T. Brooks and T. R. Roberts, Eds., Proceedings of the 9th InternationalCongress on Pesticide Chemistry, The Royal Society of Chemistry,Cambridge, 1999, pp. 120-133. See also U.S. Pat. No. 3,235,361, Col. 6,line 16 through Col. 7, line 19 and Examples 1041; U.S. Pat. No.3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12,15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182;U.S. Pat. No. 2,891,855, Col. 3, line 66 through Col. 5, line 17 andExamples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons,Inc., New York, 1961, pp 81-96; and Hance et al., Weed Control Handbook,8th Ed., Blackwell Scientific Publications, Oxford, 1989.

In the following Examples, all percentages are by weight and allformulations are prepared in conventional ways. Compound numbers referto compounds in Index Table A.

Example A

Wettable Powder Compound 1 65.0% dodecylphenol polyethylene glycol ether2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0%montmorillonite (calcined) 23.0%.

Example B

Granule Compound 1 10.0% attapulgite granules (low volatile matter,90.0%. 0.71/0.30 mm; U.S.S. No. 25-50 sieves)

Example C

Extruded Pellet Compound 1 25.0% anhydrous sodium sulfate 10.0% crudecalcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0%calcium/magnesium bentonite 59.0%.

Example D

Emulsifiable Concentrate Compound 1 20.0% blend of oil solublesulfonates 10.0% and polyoxyethylene ethers isophorone 70.0%.

Example E

Granule Compound 1 0.5% cellulose 2.5% lactose 4.0% cornmeal 93.0%.

Compounds of this invention are characterized by favorable metabolicand/or soil residual patterns and exhibit activity controlling aspectrum of agronomic and non-agronomic invertebrate pests. (In thecontext of this disclosure “invertebrate pest control” means inhibitionof invertebrate pest development (including mortality) that causessignificant reduction in feeding or other injury or damage caused by thepest; related expressions are defined analogously.) As referred to inthis disclosure, the term “invertebrate pest” includes arthropods,gastropods and nematodes of economic importance as pests. The term“arthropod” includes insects, mites, spiders, scorpions, centipedes,millipedes, pill bugs and symphylans. The term “gastropod” includessnails, slugs and other Stylommatophora. The term “nematode” includesall of the helminths, such as: roundworms, heartworms, and phytophagousnematodes (Nematoda), flukes (Tematoda), Acanthocephala, and tapeworms(Cestoda). Those skilled in the art will recognize that not allcompounds are equally effective against all pests. Compounds of thisinvention display activity against economically important agronomic andnonagronomic pests. The term “agronomic” refers to the production offield crops such as for food and fiber and includes the growth of cerealcrops (e.g., wheat, oats, barley, rye, rice, maize), soybeans, vegetablecrops (e.g., lettuce, cabbage, tomatoes, beans), potatoes, sweetpotatoes, grapes, cotton, and tree fruits (e.g., pome fruits, stonefruits and citrus fruits). The term “nonagronomic” refers to otherhorticultural (e.g., forest, greenhouse, nursery or ornamental plantsnot grown in a field), public (human) and animal health, domestic andcommercial structure, household, and stored product applications orpests. For reason of invertebrate pest control spectrum and economicimportance, protection (from damage or injury caused by invertebratepests) of agronomic crops of cotton, maize, soybeans, rice, vegetablecrops, potato, sweet potato, grapes and tree fruit by controllinginvertebrate pests are preferred embodiments of the invention. Agronomicor nonagronomic pests include larvae of the order Lepidoptera, such asarmyworms, cutworms, loopers, and heliothines in the family Noctuidae(e.g., fall armyworm (Spodoptera fugiperda J. E. Smith), beet armyworm(Spodoptera exigua Hübner), black cutworm (Agrotis ipsilon Huflagel),cabbage looper (Trichoplusia ni Hübner), tobacco budworm (Heliothisvirescens Fabricius)); borers, casebearers, webworms, coneworms,cabbageworms and skeletonizers from the family Pyralidae (e.g., Europeancorn borer (Ostrinia nubilalis Hübner), navel orangeworm (Amyeloistransitella Walker), corn root webworm (Crambus caliginosellus Clemens),sod webworm (Herpetogramma licarsisalis Walker)); leafrollers, budworms,seed worms, and fruit worms in the family Tortricidae (e.g., codlingmoth (Cydia pomonella Linnaeus), grape berry moth (Endopiza viteanaClemens), oriental fruit moth (Grapholita molesta Busck)); and manyother economically important lepidoptera (e.g., diamondback moth(Plutella xylostella Linnaeus), pink bollworm (Pectinophora gossypiellaSaunders), gypsy moth (Lymantria dispar Linnaeus)); nymphs and adults ofthe order Blattodea including cockroaches from the families Blattellidaeand Blattidae (e.g., oriental cockroach (Blatta orientalis Linnaeus),Asian cockroach (Blatella asahinai Mizukubo), German cockroach(Blattella germanica Linnaeus), brownbanded cockroach (Supellalongipalpa Fabricius), American cockroach (Periplaneta americanaLinnaeus), brown cockroach (Periplaneta brunnea Burmeister), Madeiracockroach (Leucophaea maderae Fabricius)); foliar feeding larvae andadults of the order Coleoptera including weevils from the familiesAnthribidae, Bruchidae, and Curculionidae (e.g., boll weevil (Anthonomusgrandis Boheman), rice water weevil (Lissorhoptrus oryzophilus Kuschel),granary weevil (Sitophilus granarius Linnaeus), rice weevil (Sitophilusoryzae Linnaeus)); flea beetles, cucumber beetles, rootworms, leafbeetles, potato beetles, and leafminers in the family Chrysomelidae(e.g., Colorado potato beetle (Leptinotarsa decemlineata Say), westerncorn rootworm (Diabrotica virgifera virgifera LeConte)); chafers andother beetles from the family Scaribaeidae (e.g., Japanese beetle(Popillia japonica Newman) and European chafer (Rhizotrogus majalisRazoumowsky)); carpet beetles from the family Dermestidae; wirewormsfrom the family Elateridae; bark beetles from the family Scolytidae andflour beetles from the family Tenebrionidae. In addition agronomic andnonagronomic pests include: adults and larvae of the order Dermapteraincluding earwigs from the family Forficulidae (e.g., European earwig(Forficula auricularia Linnaeus), black earwig (Chelisoches morioFabricius)); adults and nymphs of the orders Hemiptera and Homopterasuch as, plant bugs from the family Miridae, cicadas from the familyCicadidae, leafhoppers (e.g. Empoasca spp.) from the familyCicadellidae, planthoppers from the families Fulgoroidae andDelphacidae, treehoppers from the family Membracidae, psyllids from thefamily Psyllidae, whiteflies from the family Aleyrodidae, aphids fromthe family Aphididae, phylloxera from the family Phylloxeridae,mealybugs from the family Pseudococcidae, scales from the familiesCoccidae, Diaspididae and Margarodidae, lace bugs from the familyTingidae, stink bugs from the family Pentatomidae, cinch bugs (e.g.,Blissus spp.) and other seed bugs from the family Lygaeidae, spittlebugsfrom the family Cercopidae squash bugs from the family Coreidae, and redbugs and cotton stainers from the family Pyrrhocoridae. Also includedare adults and larvae of the order Acari (mites) such as spider mitesand red mites in the family Tetranychidae (e.g., European red mite(Panoychus ulmi Koch), two spotted spider mite (Tetraychus urticaeKoch), McDaniel mite (Tetranychus mcdanieli McGregor)), flat mites inthe family Tenuipalpidae (e.g., citrus flat mite (Brevipalpus lewisiMcGregor)), rust and bud mites in the family Eriophyidae and otherfoliar feeding mites and mites important in human and animal health,i.e. dust mites in the family Epidermoptidae, follicle mites in thefamily Demodicidae, grain mites in the family Glycyphagidae, ticks inthe order Ixodidae (e.g., deer tick (Ixodes scapularis Say), Australianparalysis tick (Ixodes holocyclus Neumann), American dog tick(Dermacentor variabilis Say), lone star tick (Amblyomma americanumLinnaeus) and scab and itch mites in the families Psoroptidae,Pyemotidae, and Sarcoptidae; adults and immatures of the orderOrthoptera including grasshoppers, locusts and crickets (e.g., migratorygrasshoppers (e.g., Melanoplus sanguinipes Fabricius, Ad. differentialisThomas), American grasshoppers (e.g., Schistocerca americana Drury),desert locust (Schistocerca gregaria Forskal), migratory locust (Locustamigratoria Liimaeus), house cricket (Acheta domesticus Linnaeus), molecrickets (Gryllotalpa spp.)); adults and immatures of the order Dipteraincluding leafminers, midges, fruit flies (Tephritidae), frit flies(e.g., Oscinella frit Linnaeus), soil maggots, house flies (e.g., Muscadomestica Linnaeus), lesser house flies (e.g., Fannia canicularisLinnaeus, F. femoralis Stein), stable flies (e.g., Stomoxys calcitransLinnaeus), face flies, horn flies, blow flies (e.g., Chrysomya spp.,Phormia spp.), and other muscoid fly pests, horse flies (e.g., Tabanusspp.), bot flies (e.g., Gastrophilus spp., Oestrus spp.), cattle grubs(e.g., Hypoderma spp.), deer flies (e.g., Chrysops spp.), keds (e.g.,Melophagous ovinus Linnaeus) and other Brachycera, mosquitoes (e.g.,Aedes spp., Anopheles spp., Culex spp.), black flies (e.g., Prosimuliumspp., Simulium spp.), biting midges, sand flies, sciarids, and otherNematocera; adults and immatures of the order Thysanoptera includingonion thrips (Thrips tabaci Lindeman) and other foliar feeding thrips;insect pests of the order Hymenoptera including ants (e.g., redcarpenter ant (Camponotus ferrugineus Fabricius), black carpenter ant(Camponotus pennsylvanicus De Geer), Pharaoh ant (Monomorium pharaonisLinnaeus), little fire ant (Wasmannia auropunctata Roger), fire ant(Solenopsis genlinata Fabricius), red imported fire ant (Solenopsisinvicta Buren), Argentine ant (Iridomyrnex humilis Mayr), crazy ant(Paratrechina longicornis Latreille), pavement ant (Tetramoriumcaespitum Linnaeus), cornfield ant (Lasius alienus Förster), odoroushouse ant (Tapinoma sessile Say)), bees (including carpenter bees),hornets, yellow jackets and wasps; insect pests of the order Isopteraincluding the eastern subterranean termite (Reticuliternes flavipesKollar), western subterranean termite (Reticulitermes hesperus Banks),Formosan subterranean termite (Coptotermes formosanus Shiraki), WestIndian drywood termite (Incisitermes immigrans Snyder) and othertermites of economic importance; insect pests of the order Thysanurasuch as silverfish (Lepisma saccharina Linnaeus) and firebrat (Thermobiadomestica Packard); insect pests of the order Mallophaga and includingthe head louse (Pediculus humanus capitis De Geer), body louse(Pediculus humanus humanus Linnaeus), chicken body louse (Menacanthusstramineus Nitszch), dog biting louse (Trichodectes canis De Geer),fluff louse (Goniocotes gallinae De Geer), sheep body louse (Bovicolaovis Schrank), short-nosed cattle louse (Haematopinus eurysternusNitzsch), long-nosed cattle louse (Linognathus vituli Linnaeus) andother sucking and chewing parasitic lice that attack man and animals;insect pests of the order Siphonoptera including the oriental rat flea(Xenopsylla cheopis Rothschild), cat flea (Ctemocephalides felisBouche), dog flea (Ctenocephalides canis Curtis), hen flea(Ceratophyllus gallinae Schrank), sticktight flea (Echidnophagagallinacea Westwood), human flea (Pulex irritans Linnaeus) and otherfleas afflicting mammals and birds. Additional arthropod pests coveredinclude: spiders in the order Araneae such as the brown recluse spider(Loxosceles reclusa Gertsch & Mulaik) and the black widow spider(Latrodectus mactans Fabricius), and centipedes in the orderScutigeromorpha such as the house centipede (Scuttigera coleoptrataLinnaeus). Compounds of the present invention also have activity onmembers of the Classes Nernatoda, Cestoda, Trematoda, and Acanthocephalaincluding economically important members of the orders Strongylida,Ascaridida, Oxyurida, Rhabditida, Spilurida, and Enoplida such as butnot limited to economically important agricultural pests (i.e. root knotnematodes in the genus Meloidogyne, lesion nematodes in the genusPratylenchus, stubby root nematodes in the genus Trichodorus, etc.) andanimal and human health pests (i.e. all economically important flukes,tapeworms, and roundworms, such as Strongylus vulgaris in horses,Toxocara canis in dogs, Haemonchus contortus in sheep, Dirofilariaimmitis Leidy in dogs, Anoplocephala perfoliata in horses, Fasciolahepatica Linnaeus in ruminants, etc.).

Compounds of the invention show particularly high activity against pestsin the order Lepidoptera (e.g., bama argillacea Hübner (cotton leafworm), Archips argyrospila Walker (fruit tree leaf roller), A. rosanaLinnaeus (European leaf roller) and other Archips species, Chilosuppressalis Walker (rice stem borer), Cnaphalocrosis medinalis Guenee(rice leaf roller), Crambus caliginosellus Clemens (corn root webworm),Crambus teterellus Zincken (bluegrass webworm), Cydia pomonella Linnaeus(codling moth), Earias insulana Boisduval (spiny bollworm), Eariasvittella Fabricius (spotted bollworm), Helicoverpa armigera Hübner(American bollworm), Helicoverpa zea Boddie (corn earworm). Heliothisvirescens Fabricius (tobacco budworm), Herpetogramma licarsisalis Walker(sod webworm), Lobesia botrana Denis & Schiffermüller (grape berrymoth), Pectinophora gossypiella Saunders (pink bollworm), Phyllocnistiscitrella Stainton (citrus leafminer), Pieris brassicae Linnaeus (largewhite butterfly), Pieris rapae Linnaeus (small white butterfly),Plutella xylostella Limiaeus (diamondback moth), Spodoptera exiguaHübner (beet armyworm), Spodoptera litura Fabricius (tobacco cutworm,cluster caterpillar), Spodoptera frugiperda J. E. Smith (fall almyworm),Trichoplusia ni Hübner (cabbage looper) and Tutta absoluta Meyrick(tomato leafminer)). Compounds of the invention also have commerciallysignificant activity on members from the order Homoptera including:Acyrthisiphon pisum Harris (pea aphid), Aphis craccivora Koch (cowpeaaphid), Aphis fabae Scopoli (black bean aphid), Aphis gossypii Glover(cotton aphid, melon aphid), Aphis pomi De Geer (apple aphid), Aphisspiraecola Patch (spirea aphid), Aulacorthum solani Kaltenbach (foxgloveaphid), Chaetosiphon fragaefolii Cockerell (strawvberry aphid),Diuraphis noxia Kurdjumov/Mordvilko (Russian wheat aphid), Dysaphisplantaginea Paaserini (rosy apple aphid), Eriosoma lanigerum Hausmann(woolly apple aphid), Hyalopterus pruni Geoffroy (mealy plum aphid),Lipaphis erysimi Kaltenbach (turnip aphid), Metopolophium dirrhodumWalker (cereal aphid), Macrosipum euphorbiae Thomas (potato aphid),Myzus persicae Sulzer (peach-potato aphid, green peach aphid), Nasonoviaribisnigri Mosley (lettuce aphid), Pemphigus spp. (root aphids and gallaphids), Rhopalosiphum maidis Fitch (corn leaf aphid), Rhopalosiphumpadi Linnaeus (bird cherry-oat aphid), Schizaphis gramimum Rondani(greenbug), Sitobion avenzae Fabricius (English grain aphid),Therioaphis maculata Buckton (spotted alfalfa aphid), Toxoptera aurantiiBoyer de Fonscolombe (black citrus aphid), and Toxoptera citricidaKirkaldy (brown citrus aphid); Adelges spp. (adelgids); Phylloxeradevastatrix Pergande (pecan phylloxera); Bemisia tabaci Gennadius(tobacco whitefly, sweetpotato whitefly), Bemisia argentifolii Bellows &Perring (silverleaf whitefly), Dialeurodes citri Ashmead (citruswhitefly) and Trialeurodes vaporariorim Westwood (greenhouse whitefly);Emipoasca fabae Harris (potato leafhopper), Laodelphax striatellusFallen (smaller brown planthopper), Macrolestes quadrilineatus Forbes(aster leafhopper), Nephotettix cinticeps Uhler (green leafhopper),Nephotettix nigropictus Stal (rice leafhopper), Nilaparvata lugens Stal(brown planthopper), Pereginus maidis Ashmead (corn planthopper),Sogatella furcifera Horvath (white-backed planthopper), Sogatodesorizicola Muir (rice delphacid), Typhlocyba pomaria McAtee white appleleafhopper, Erythroneoura spp. (grape leafhoppers); Magicidadaseptendecin Linnaeus (periodical cicada); Icerya purchasi Maskell(cottony cushion scale), Quadraspidiotus perniciosus Comstock (San Josescale); Planococcus citri Risso (citrus mealybug); Pseudococcus spp.(other mealybug complex); Cacopsylla pyricola Foerster (pear psylla),Trioza diospyri Ashmead (persimmon psylla). These compounds also haveactivity on members from the order Hemiptera including: Acrosternumhilare Say (green stink bug), Anasa tristis De Geer (squash bug),Blissus leucopterus leucopterus Say (chinch bug), Corythuca gossypiiFabricius (cotton lace bug), Cyrtopeltis modesta Distant (tomato-bug),Dysdercus suturellus Herrich-Schaffer (cotton stainer), Euchistus selvusSay (brown stink bug), Euchistus variolarius Palisot de Beauvois(one-spotted stink bug), Graptosthetus spp. (complex of seed bugs),Leptoglossus corculus Say (leaf-footed pine seed bug), Lygus lineolarisPalisot de Beauvois (tarnished plant bug), Nezara viridula Linnaeus(southern green stink bug), Oebalus pugnax. Fabricius (rice stink bug),Oncopeltus fasciatus Dallas (large milkweed bug), Pseudatomoscelisseriatus Reuter (cotton fleahopper). Other insect orders controlled bycompounds of the invention include Thysanoptera (e.g., Frankliniellaoccidentalis Pergande (western flower thrip), Scirthothrips citriMoulton (citrus thrip), Sericothrips variabilis Beach (soybean thrip),and Thrips tabaci Lindeman (onion thrip); and the order Coleoptera(e.g., Leptinotarsa decemzlineata Say (Colorado potato beetle),Epilachna varivestis Mulsant (Mexican bean beetle) and wireworms of thegenera Agriotes, Athous or Limonius).

Compounds of this invention can also be mixed with one or more otherbiologically active compounds or agents including insecticides,fungicides, nematocides, bactericides, acaricides, growth regulatorssuch as rooting stimulants, chemosterilants, semiochemicals, repellents,attractants, pheromones, feeding stimulants, other biologically activecompounds or entomopathogenic bacteria, virus or fungi to form amulti-component pesticide giving an even broader spectrum ofagricultural utility. Thus compositions of the present invention canfurther comprise a biologically effective amount of at least oneadditional biologically active compound or agent. Examples of suchbiologically active compounds or agents with which compounds of thisinvention can be formulated are: insecticides such as abamectin,acephate, acetaniprid, avelmectin, azadirachtin, azinphos-methyl,bifenthrin, binfenazate, buprofezin, carbofuran, chlorfenapyr,chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl, chromafenozide,clothianidin, cyflutluin, beta-cyfluthrin, cyhalothrin,lambda-cyhalothrin, cypermethrin, cyromazine, deltainethlin,diafenthiuron, diazinon, diflubenzuron, dimethoate, diofenolan,emamectin, endosulfan, esfenvalerate, ethiprole, fenothicarb,fenoxycarb, fenpropathrin, fenproximate, fenvalerate, fipronil,flonicamid, flucythrinate, tau-fluvalinate, flufenoxuron, fonophos,halofenozide, hexaflumuron, imidacloprid, indoxacarb, isofenphos,lufenuron, malathion, metaldehyde, methamidophos, methidathion,methomyl, methoprene, methoxychlor, monocrotophos, methoxyrfenozide,nithiazin, novaluron, oxamyl, parathion, parathion-methyl, permethrin,phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos,pymetrozine, pyridalyl, pyriproxifen, rotenone, spinosad, sulprofos,tebufenozide, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos,thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin,trichlorfon and triflumuron; fungicides such as acibenzolar,azoxystrobin, benomyl, blasticidin-S, Bordeaux mixture (tribasic coppersulfate), bromuconazole, carpropamid, captafol, captani, carbendazim,chloroneb, chlorothalonil, copper oxychloride, copper salts,cyflufenamid, cymoxanil, cyproconazole, cyprodinil,(S)-3,5-dichloro-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)-4-methylbenzamide(RH 7281), diclocymet (S-2900), diclomezine, dicloran, difenoconazole,(S)-3,5-dihydro-5-methyl-2-(methylthio)-5-phenyl-3-(phenylamino)-4H-imidazol-4-one(RP 407213), dimethomorph, dimoxystrobin, diniconazole, diniconazole-M,dodine, edifenphos, epoxiconazole, famoxadone, fenamidone, fenarimol,fenbuconazole, fencaramid (SZX0722), fenpiclonil, fenpropidin,fenpropimorph, fentin acetate, fentin hydroxide, fluazinam, fludioxonil,flumetover (RPA 403397), fluquinconazole, flusilazole, flutolanil,flutriafol, folpet, fosetyl-aluminum, furalaxyl, furametapyr (S-82658),hexaconazole, ipconazole, iprobenfos, iprodione, isoprothiolane,kasugamycin, kresoxim-methyl, mancozeb, maneb, mefenoxam, mepronil,metalaxyl, metconazole, metomino-strobin/fenominostrobin (SSF-126),myclobutanil, neo-asozin (ferric methanearsonate), oxadixyl,penconazole, pencycuron, probenazole, prochloraz, propamocarb,propiconazole, pyrifenox, pyraclostrobin, pyrimethanil, pyroquilon,quinoxyfen, spiroxamine, sulfur, tebuconazole, tetraconazole,thiabendazole, thifluzamide, thiophanate-methyl, thiram, tiadinil,triadimefon, triadimenol, tricyclazole, trifloxystrobin, triticonazole,validamycin and vinclozolin; nematocides such as aldicarb, oxamyl andfenamiphos; bactericides such as streptomycin; acaricides such asamitraz, chinomethionat, chlorobenzilate, cyhexatin, dicofol,dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin,fenpyroximate, hexythiazox, propargite, pyridaben and tebufenpyrad; andbiological agents such as Bacillus thuringiensis including ssp. aizawaiand kurstaki, Bacillus thuringiensis delta endotoxin, baculovirus, andentomopathogenic bacteria, virus and fungi. Compounds of this inventionand compositions thereof can be applied to plants geneticallytransformed to express proteins toxic to invertebrate pests (such asBacillus thuringiensis toxin). The effect of exogenously appliedinvertebrate pest control compounds of this invention may be synergisticwith the expressed toxin proteins.

A general reference for these agricultural protectants is The PesticideManual, 12th Edition, C. D. S. Tomlin, Ed., British Crop ProtectionCouncil, Farnham, Surrey, U.K., 2000.

Preferred insecticides and acaricides for mixing with compounds of thisinvention include pyrethroids such as cypermethrin, cyhalothrin,cyfluthrin, beta-cyfluthrin, esfenvalerate, fenvalerate andtralomethrin; carbamates such as fenothicarb, methomyl, oxamyl andthiodicarb; neonicotinoids such as clothianidin, imidacloprid andthiacloprid; neuronal sodium channel blockers such as indoxacarb;insecticidal macrocyclic lactones such as spinosad, abamectin,avermectin and emamectin; γ-aminobutyric acid (GABA) antagonists such asendosulfan, ethiprole and fipronil; insecticidal ureas such asflufenoxuron and triflumuron; juvenile hormone mimics such as diofenolanand pyriproxyfen; pymetrozine; and amitraz. Preferred biological agentsfor mixing with compounds of this invention include Bacillusthuringiensis and Bacillus thuringiensis delta endotoxin as well asnaturally occurring and genetically modified viral insecticidesincluding members of the family Baculoviridae as well as entomophagousfungi.

Most preferred mixtures include a mixture of a compound of thisinvention with cyhalothrin; a mixture of a compound of this inventionwith beta-cyfluthrin; a mixture of a compound of this invention withesfenvalerate; a mixture of a compound of this invention with methomyl;a mixture of a compound of this invention with imidacloprid; a mixtureof a compound of this invention with thiacloprid; a mixture of acompound of this invention with indoxacarb; a mixture of a compound ofthis invention with abamectin; a mixture of a compound of this inventionwith endosulfan; a mixture of a compound of this invention withethiprole; a mixture of a compound of this invention with fipronil; amixture of a compound of this invention with flufenoxuron; a mixture ofa compound of this invention with pyriproxyfen; a mixture of a compoundof this invention with pymetrozine; a mixture of a compound of thisinvention with amitraz; a mixture of a compound of this invention withBacillus thuringiensis and a mixture of a compound of this inventionwith Bacillus thuringiensis delta endotoxin.

In certain instances, combinations with other invertebrate pest controlcompounds or agents having a similar spectrum of control but a differentmode of action will be particularly advantageous for resistancemanagement. Thus, compositions of the present invention can furthercomprise a biologically effective amount of at least one additionalinvertebrate pest control compound or agent having a similar spectrum ofcontrol but a different mode of action. Contacting a plant geneticallymodified to express a plant protection compound (e.g., protein) or thelocus of the plant with a biologically effective amount of a compound ofinvention can also provide a broader spectrum of plant protection and beadvantageous for resistance management.

Invertebrate pests are controlled in agronomic and nonagronomicapplications by applying one or more of the compounds of this invention,in an effective amount, to the environment of the pests including theagronomic and/or nonagronomic locus of infestation, to the area to beprotected, or directly on the pests to be controlled. Thus, the presentinvention further comprises a method for the control of an invertebratepest in agronomic and/or nonagronomic applications, comprisingcontacting the invertebrate pest or its environment with a biologicallyeffective amount of one or more of the compounds of the invention, orwith a composition comprising at least one such compound or acomposition comprising at least one such compound and an effectiveamount of at least one additional biologically active compound or agent.Examples of suitable compositions comprising a compound of the inventionand an effective amount of at least one additional biologically activecompound or agent include granular compositions wherein the additionalbiologically active compound or agent is present on the same granule asthe compound of the invention or on granules separate from those of thecompound of this invention.

A preferred method of contact is by spraying. Alternatively, a granularcomposition comprising a compound of the invention can be applied to theplant foliage or the soil. Compounds of this invention are alsoeffectively delivered through plant uptake by contacting the plant witha composition comprising a compound of this invention applied as a soildrench of a liquid formulation, a granular formulation to the soil, anursery box treatment or a dip of transplants. Compounds are alsoeffective by topical application of a composition comprising a compoundof this invention to the locus of infestation. Other methods of contactinclude application of a compound or a composition of the invention bydirect and residual sprays, aerial sprays, gels, seed coatings,microencapsulations, systemic uptake, baits, eartags, boluses, foggers,fumigants, aerosols, dusts and many others. The compounds of thisinvention may also be impregnated into materials for fabricatinginvertebrate control devices (e.g. insect netting).

The compounds of this invention can be incorporated into baits that areconsumed by the invertebrates or within devices such as traps and thelike. Granules or baits comprising between 0.01-5% active ingredient,0.05-10% moisture retaining agent(s) and 40-99% vegetable flour areeffective in controlling soil insects at very low application rates,particularly at doses of active ingredient that are lethal by ingestionrather than by direct contact.

The compounds of this invention can be applied in their pure state, butmost often application will be of a formulation comprising one or morecompounds with suitable carriers, diluents, and surfactants and possiblyin combination with a food depending on the contemplated end use. Apreferred method of application involves spraying a water dispersion orrefined oil solution of the compounds. Combinations with spray oils,spray oil concentrations, spreader stickers, adjuvants, other solvents,and synergists such as piperonyl butoxide often enhance compoundefficacy.

The rate of application required for effective control (i.e.“biologically effective amount”) will depend on such factors as thespecies of invertebrate to be controlled, the pest's life cycle, lifestage, its size, location, time of year, host crop or animal, feedingbehavior, mating behavior, ambient moisture, temperature, and the like.Under normal circumstances, application rates of about 0.01 to 2 kg ofactive ingredient per hectare are sufficient to control pests inagronomic ecosystems, but as little as 0.0001 kg/hectare may besufficient or as much as 8 kg/hectare may be required. For nonagronomicapplications, effective use rates will range from about 1.0 to 50mg/square meter but as little as 0.1 mg/square meter may be sufficientor as much as 150 mg/square meter may be required. One skilled in theart can easily determine the biologically effective amount necessary forthe desired level of invertebrate pest control.

The following TESTS demonstrate the control efficacy of compounds ofthis invention on specific pests. “Control efficacy” representsinhibition of invertebrate pest development (including mortality) thatcauses significantly reduced feeding. The pest control protectionafforded by the compounds is not limited, however, to these species. SeeIndex Tables A and B for compound descriptions. The followingabbreviations are used in the Index Tables that follow: “Me” meansmethyl, “i” means iso, “Pr” means propyl and i-Pr means isopropyl. Theabbreviation “Ex.” stands for “Example” and is followed by a numberindicating in which example the compound is prepared.

INDEX TABLE A

Compound R⁴ R³ J m.p. ° C. 1 Me i-Pr 4-Cl-phenyl 208-210 2 (Ex. 2) Mei-Pr 1-(3-Cl-2-pyridinyl)-3-CF₃- 69-72 5-pyrazolyl

INDEX TABLE B

Compound R⁴ R³ J m.p. ° C. B1 Me i-Pr 4-CF₃-phenyl 139-142 B2 (Ex. 1) Mei-Pr 4-OCF₃-phenyl 104-107 B3 Me i-Pr 1-(3-Cl-2-pyridinyl)-3-CF₃- 69-735-pyrazolyl

INDEX TABLE C

Compound R⁴ R³ J m.p. ° C. C1 Me i-Bu 1-(3-Cl-2-pyridinyl)-3-CF₃-138-140 5-pyrazolyl C2 (Ex. 3) Me i-Bu 1-(3-Cl-2-pyridinyl)-3-Br-119-120 5-pyrazolyl C3 Me Et 1-(3-Cl-2-pyridinyl)-3-Br- 185-1865-pyrazolyl C4 Me Me 1-(3-Cl-2-pyridinyl)-3-Br- 133-135 5-pyrazolyl C5Me Me 1-(3-Cl-2-pyridinyl)-3-CF₃- 113-114 5-pyrazolyl C6 Me i-Pr1-(3-Cl-2-pyridinyl)-3-Br- 102-104 5-pyrazolyl C7 Me i-Pr1-(3-Cl-2-pyridinyl)-3-CF₃- 124-125 5-pyrazolyl

INDEX TABLE D

Compound R⁴ R³ J m.p. ° C. D1 Me Et 1-(3-Cl-2-pyridinyl)-3-Br- 152-1545-pyrazolyl D2 Me Me 1-(3-Cl-2-pyridinyl)-3-Br- 181-182 5-pyrazolyl

BIOLOGICAL EXAMPLES OF THE INVENTION

For evaluating control of diamondback moth (Plutella xylostella) thetest unit consisted of a small open container with a 12-14-day-oldradish plant inside. This was pre-infested with 10-15 neonate larvae ona piece of insect diet by use of a core sampler to remove a plug from asheet of hardened insect diet having many larvae growing on it andtransfer the plug containing larvae and diet to the test unit. Thelarvae moved onto the test plant as the diet plug dried out.

Test compounds were formulated using a solution containing 10% acetone,90% water and 300 ppm X-77® (D Spreader Lo-Foam Formula non-ionicsurfactant containing alkylarylpolyoxyethylene, free fatty acids,glycols and isopropanol (Loveland Industries, Inc.), unless otherwiseindicated. The formulated compounds were applied in 1 mL of liquidthrough a SUJ2 atomizer nozzle with ⅛ JJ custom body (Spraying SystemsCo.) positioned 1.27 cm (0.5 inches) above the top of each test unit.All experimental compounds in this screen were sprayed at 250 ppm (orlower) and replicated three times. After spraying of the formulated testcompound, each test unit was allowed to dry for 1 hour and then a black,screened cap was placed on top. The test units were held for 6 days in agrowth chamber at 25° C. and 70% relative humidity. Plant feeding damagewas then visually assessed.

Of the compounds tested, the following provided excellent levels ofplant protection (20% or less feeding damage): 1*, B3*, C2**, C5* andC6*.

Test B

For evaluating control of fall armyworm (Spodoptera frugiperda) the testunit consisted of a small open container with a 45-day-old corn (maize)plant inside. This was pre-infested with 10-15 1-day-old larvae on apiece of insect diet by use of a core sampler as described for Test A.

Test compounds were formulated and sprayed at 250 ppm (or lower) asdescribed for Test A. The applications were replicated three times.After spraying, the test units were maintained in a growth chamber andthen visually rated as described for Test A.

Of the compounds tested, the following provided excellent levels ofplant protection (20% or less feeding damage): C2* and C5*.

Test C

For evaluating control of tobacco budworm (Heliothis virescens) the testunit consisted of a small open container with a 6-7 day old cotton plantinside. This was pre-infested with 8 2-day-old larvae on a piece ofinsect diet by use of a core sampler as described for Test A.

Test compounds were formulated and sprayed at 250 ppm (or lower) asdescribed for Test A. The applications were replicated three times.After spraying, the test units were maintained in a growth chamber andthen visually rated as described for Test A.

Of the compounds tested, the following provided excellent levels ofplant protection (20% or less feeding damage): C2* and C6*.

*Tested at 50 ppm.

**Tested at 10 ppm.

1. A compound of Formula 2, an N-oxide or a salt thereof

wherein R³ is i-propyl or methyl; R^(4a) is methyl or Cl; R^(4b) is H,Cl or Br; provided that (a) when R^(4a) is methyl and R^(4b) is H, thenR³ is not i-propyl; and (b) when R^(4a) is Cl, then R^(4b) is Br.
 2. Thecompound of claim 1 wherein R³ is methyl, R^(4a) is methyl and R^(4b) isH.
 3. The compound of claim 1 wherein R³ is methyl, R^(4a) is methyl andR^(4b) is Cl.